Last year, I recapped how my husband and I racked up 175,000 points in a year. We didn’t turn to sign-up bonuses, expensive purchases, or even strategically spend on cards that 5x the points instead of 4x the points.

I shared in as much detail as I could, because I wanted to show that travel made possible by points is possible. It just takes a little upfront work—once you have a system in place, the miles come flooding in.

Since then, we’ve drastically shifted our strategy: We now own a home, needed a new airline-adjacent card, and we weren’t using others. We primarily use Bilt for housing, American Express (currently up to 175k sign-up bonus for the Platinum) and Chase (currently up to 100k sign-up bonus for the Preferred or the Reserve) for everyday spending, and Rakuten for cash back when shopping (referral links).

I wasn’t ultimately sure if our approach was as optimized as possible anymore, so I asked an expert to take a look.

Ashley Feinstein Gerstley is Rakuten’s Shopping and Savings Strategist, in addition to being a Certified Financial Professional®, so she knows a thing or two about creating a smart financial foundation and leveraging it to power travel. Plus, I welcomed her thoughts as someone who works intimately with a product I use everyday—and a big cornerstone of our strategy: Rakuten.

If you’re unfamiliar, Rakuten gives you cash back when you shop online, sent via check or direct deposit several times a year. They partner with thousands of brands you likely regularly visit—from CVS to Hotels.com, Sephora to PetSmart. Upon switching from cash back to their AmEx partnership (where you can earn Membership Rewards), we’ve earned 189,940 points. Not bad for shopping I was doing anyway.

If you’re nosy like me, I hope you enjoy this look “under the hood” at my own strategy, as well my conversation with Ashley on how to best use Rakuten, the best times of year for certain deals, and how she uses Rakuten for her own business class trips.

Ashley, you’re a CFP® and you run The Fiscal Femme (which I knew of from my time at Money with Katie!). As a CFP® professional, you’re also a fiduciary, meaning you must always act in a client’s best financial interests. I’m curious: If someone has their financial life in a stable place (they have an emergency fund, they’re paying off debts, they have some expendable income), where does strategizing around points/miles fall in your prioritization hierarchy? Is it a worthwhile use of time for most folks, or more for nerds like me who enjoy this stuff?

This is such a great question. I’d say it’s so personal. Points/miles strategizing can be such a practical way to get more from the money you do spend. I’m able to travel more than I would otherwise and in a way I wouldn’t be able to otherwise by using these strategies, so it’s a pretty significant lever for our family.

In a couple of weeks, our family of four is heading to Italy on an Emirates flight that we paid for using points. We typically take an international trip with the kids once per year where our flights are covered by points. We’re also planning a trip to Japan using points and are hoping to fly business class. My oldest son flew business class once (paid for by points), and I think it was the highlight of his trip.

On the flip-side, I also know it can feel like a significant investment of time and overwhelming for some. This is where I think it’s helpful to have an experienced expert who can share simple strategies and tips for the most important things to prioritize to make an impact. Things like spending more than you would otherwise or taking on additional debt are not what I would advise. It’s about being really intentional and strategic.

This year, our approach to earning points has shifted a bit, and we’ve earned 275,000 points by July 1st. I’d love to outline it below and get your thoughts on my strategy. Where else can I optimize? What holes do you see? Or, conversely, am I over-optimizing?

• Bilt now offers points on mortgages, as long as your daily spend parallels that cost. For example, if your mortgage is $5,000 (close to our actual scenario) and you spend $3,750 in additional daily spend (75% of your housing cost), you’ll earn 5,000 points plus the additional 3,750 points, for a total of 8,750 points a month. So far in 2026, we have earned 37,000 points here. For context, we use the Bilt Blue Card because we didn’t want to pay another high annual fee on top of our Chase Sapphire Reserve and American Express Platinum.

• Once we reach that threshold for Bilt, we’ll move our spending to one of those two cards, as both platforms have exceptionally valuable points and transfer partners, in addition to programs like Points Boost and the Fine Hotel + Resorts Program. So far, we have racked up 93,000 points on Chase (the large majority came through referrals, travel bookings, and Lyft), and 38,000 from American Express, 14,800 of which came from Rakuten.

• Because we no longer live in a United hub and are now primarily flying on Delta, we downgraded our United cards and opened a Delta card that had a 85,000 point sign-up bonus if we spent $4,000 in six months. We had to purchase two large items anyway, so we’re on track to earn that 85,000 this month.

• I also religiously use Rakuten for any online shopping, so I have another 22,000 points waiting for us during the next Membership Rewards day in August.

• In total, that’s 275,000 points, with the other half of the year to go, where we project to earn another 40,000 from Bilt and 40,000 from other spending combined across Rakuten, Chase, and American Express.

I love the intentionality of your approach. Reading through, I was struck by how similarly we’ve set up our systems.

• Earning points on your mortgage is major.

• Timing the Delta sign-up bonus around purchases you already had planned is such a smart move.

• Swapping your United card for Delta given where you live and who you’re flying with is a savvy strategic choice.

• You are optimizing purchases by religiously using Rakuten. It’s all paying off.

As to where you could optimize, I’d run a fee audit. Once the sign-up bonuses are earned, it’s helpful to confirm the annual costs are still worth it and to calculate the value you’re getting from each card. On the flip-side, given your Bilt card use, you can also evaluate if you’d get more benefit from upgrading there. I am with you in that I only want to pay for cards with a high annual fee when it’s worth it.

I’d also keep an eye on the redemption side. Points tend to lose value over time, so I’m an earn-and-burn person, meaning I make plans to use my points within a reasonable time frame.

I resonated with what you shared in your write-up about not agonizing over optimal spending. That life is also not for me, but for any large recurring or one-time expenses, it can be impactful to optimize. Much like your choice to prioritize hitting the Delta sign-up bonus.

As far as over-optimizing, I don’t see that. Your approach is dialed in, rather than obsessive.

For someone planning a few trips a year (not 10+), how would you scale down my strategy? What's the "starter kit" version of what my husband and I are doing?

When I think about a “starter kit,” I gravitate toward larger key decisions and habits that can have the most impact:

• First, I’d get the Rakuten browser extension so that cash back opportunities are flagged for you automatically when you’re shopping online. Over time, as you see the impact, checking cash back becomes a habit, and you start factoring it into your decision-making.

• From there, I’d start with one card in an ecosystem that matches how you already travel or plan to travel. Put your everyday spending on it and pay it off in full each month.

• If you can time a sign-up bonus around spending you already have coming, even better.

  

I read a survey* from your team at Rakuten and The Harris Poll that says nearly half of shoppers (49%) forget to apply rewards when they check out. It’s a missed opportunity, and it got me wondering: What other checkout habits are costing shoppers money every week that are easy to shift/implement?

Beyond forgetting to activate rewards, another common habit that costs shoppers money is checking out without comparing offers. Many shoppers default to the first retailer they find, but the same item may be available for less elsewhere, and Cash Back rates can differ by retailer. Before you complete your purchase, take a minute to check Rakuten to find the best combination of price and Cash Back. It's a simple step that makes a noticeable difference over time.

As a recent example, when I was booking our hotels for our upcoming Italy trip, I saw that the various booking sites offered similar room rates and perks, but the cash back on Expedia vs. Booking.com vs. Orbitz varied significantly. I’m always looking for the best all-in deal.

Let’s talk stacking promotions: I’ll often see a sale on a site like Farm Rio, and then see they have a Rakuten cash-back offer for an additional 15%, so I’m able to pay the lowest cost and get a nice boost in points. How often does that happen across retailers? Is it something more shoppers should be keeping an eye out on? What else is worth knowing about points stacking?

It happens more often than people realize, especially during major shopping moments like back-to-school season, Labor Day, and Black Friday. Retailers frequently run their own sales while Rakuten is simultaneously offering Cash Back, giving shoppers the opportunity to stack both and maximize their savings on the same purchase.

The best part about stacking is that shoppers don’t have to choose between a great sale price and earning rewards. While shoppers often run into restrictions like “cannot be combined with other offers” when using promo codes or coupons, Rakuten Cash Back can be applied on top of a retailer’s own discount or promotional sale, allowing shoppers to save on the sale price while still earning Cash Back.

The key is to check Rakuten before making a purchase, especially during major shopping moments when Cash Back rates are often boosted.

Beyond the obvious (browser extensions, checking before purchases, etc.), what's a Rakuten feature or trick most people don't know about? I have the app on my phone as well, but I’m never quite as good at using it when I’m in a store!

One feature many shoppers don’t take full advantage of is Rakuten’s in-store Cash Back offers, like you mentioned. While most people think of Rakuten for online shopping, the app can also help you discover offers from participating retailers when you’re shopping in person. This is especially helpful for everyday trips to places like CVS, Target, and other retailers where you’re already picking up essentials, as well as those spontaneous small shopping sprees. Before making a purchase, it’s worth checking the app to see if you can earn Cash Back on items you were planning to buy anyway.

Another lesser-known trick (that you’ve also mentioned) is that shoppers don’t have to take their Rakuten rewards as Cash Back. By linking an eligible American Express card that earns Membership Rewards, shoppers can choose to receive their Rakuten earnings as American Express points instead. This allows everyday purchases made through Rakuten to help build up points that can be used toward travel and other rewards.

Our family has earned thousands in cash back using Rakuten over time and I’ve only become a super user in the last few years. After reading through your strategies though, I’m leaning towards switching my cash back for points!

A few months ago I was at the park gushing to a friend about Rakuten, and a woman came up to me and shared that she used Rakuten to book her sister’s bachelorette and it almost paid for her entire portion of the trip. When we use it for big travel purchases, the benefits stack up quickly.

Last fall, Rakuten launched a partnership with Bilt Points, similar to the one they have with American Express’s Membership Rewards. How do you decide which program to use (or do you think the cash-back option is the best one entirely)? I primarily look at having a mix of points in all categories, keeping an eye on transfer partners I might want to use in the next couple months, but I’m not always running the math, which might be leaving some value on the table. Can you share how you’d approach it?

There’s no one-size-fits-all answer. It really depends on what you’re working toward. I always encourage shoppers to start with their end goal.

If you’re planning a trip and know you’ll redeem points through a specific airline or hotel transfer partner, earning American Express Rewards or Bilt Points through Rakuten may help you get more value from those purchases. For example, Bilt points generally hold a higher per point valuation with World of Hyatt and American Airlines. If you don’t have a redemption in mind, Cash Back offers the most flexibility since you can use it however you’d like via PayPal or check. You can get your cash back through PayPal to use that money however you’d like.

It’s also worth taking note of where you already have points. If it’s spread across several programs, it may make sense to concentrate your earnings in the program that will help you reach your next redemption faster, rather than slowly accumulating small balances everywhere.

On the other hand, if you’re close to earning enough points for a flight or hotel stay, directing your Rakuten rewards there can help you get over the finish line sooner. Ultimately, the best strategy is to be intentional!

This newsletter is primarily written for women, and we’re often the ones deploying our household’s purchasing power. Do you find that women are also more diligent when it comes to savings via programs like Rakuten? What's the most common blind spot you see in how women approach reward spending?

Rakuten and The Harris Poll actually released data* earlier this year that shows maximizing rewards has become a priority for shoppers across the board, regardless of gender. When it comes to big purchases, women are slightly more likely to say they strategically maximize rewards, with 78% saying they do so compared to 75% of men. And when asked whether they’re prioritizing rewards more than ever, men and women responded equally, with 74% of both groups saying rewards are playing a bigger role in their shopping decisions.

Regardless, what this tells me is women are being smart, strategic and thoughtful about saving. These small habits add up and over time help to build a financial muscle that influences smart financial decision-making across the board.

Slow travel here means longer stays, fewer flights, more time in one place. Does that change how you'd advise someone to prioritize points, maybe more toward hotel loyalty and long-stay perks, versus airline miles (which is what I’d usually lean towards)?

Slow travel is a great example of how shoppers can rethink the way they maximize rewards. If you’re taking fewer flights and spending more time in one destination, it may make sense to look beyond just airline miles and take advantage of opportunities to earn on hotels, vacation rentals, rental cars, and other travel-related purchases through Rakuten.

Whether you’re booking a longer hotel stay through partners like Expedia, Priceline, or IHG Hotels & Resorts, or planning a road trip with a rental car company like Hertz, there are opportunities to earn Cash Back on travel expenses you’re already planning to make.

That said, the best rewards strategy comes down to your personal travel habits. Rakuten data shows that 43% of shoppers use travel purchases as a way to earn rewards, while 53% use rewards to help fund travel. Whether you’re earning Cash Back to put toward a future getaway or redeeming those rewards to offset the cost of an upcoming trip, Rakuten is a great tool for reaching your travel goals.

Similar to slow travel, I’m also passionate about slow fashion and not spending just to spend. At the same time, there are items we’ll need throughout the year that we can plan for—you once said Memorial Day is a peak time for travel gear and hotel stays to be heavily discounted. Do you have any insights on what might be on the horizon for shoppers or travelers in the coming months?

I always encourage shoppers to be intentional and think ahead about purchases they know they’ll need throughout the year. Labor Day is a great example of a seasonal shopping moment where consumers can find value on items they were already planning to buy. It’s a smart time to shop for back-to-school clothing and refresh fall wardrobes, as well as outdoor furniture as retailers transition out of summer inventory.

For travel specifically, if timing aligns, I try to book during Rakuten’s promotional events like Big Stack and Big Give Week where cash back on travel can be upwards of 10–15%. You can also look out for boosted rates throughout the year. January also tends to be a great time to book travel because post holiday demand drops sharply. For travel to locations during peak times, I try to book further in advance. If I’m more flexible with location and dates, I often look for last minute deals.

Sign up for loyalty programs with travel booking sites so you’re alerted to their promotions and deals. They often run promotions in summer and then another round in the fall on “Travel Tuesday” (after Black Friday/Cyber Monday). A lot of it comes down to getting familiar with pricing so you can watch it over time and grab a great deal.

Anything I didn’t ask that you’d love to cover or any final tips you want to share?

Have fun with it if you can. Points and miles might sound like homework, but this is one of the rare corners of personal finance where the payoff is a trip you get to dream about and enjoy.

Celebrate the wins along the way, whether that's shopping with Rakuten, seeing a sign-up bonus hit your account, or realizing you just flew your family somewhere for close-to-free. And if you want to keep in touch, you can find me on Substack at @thefiscalfemme: .

*Survey Methodology: This survey was conducted online within the United States by The Harris Poll on behalf of Rakuten (or Autumn Communications) from Mar 24 - 26, 2026, among 2,098 adults ages 18 and older. The sampling precision of Harris online polls is measured by using a Bayesian credible interval. For this study, the sample data is accurate to within +/- 2.7 percentage points using a 95% confidence level. For complete survey methodology, including weighting variables and subgroup sample sizes, please contact Nora Rabie at nora@autumncommunications.com.

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• 📺 Starting in early August, Netflix is partnering with publishers like Condé Nast and Hearst to bring short-form video content to your streaming, and travel PR agencies are taking notice. But I’m curious if this will lead to additional over-tourism of the same places that have been struggling for years, or if will give reporters a chance to go deeper into newer, slower travel. Here’s hoping for the latter.

• 🙂‍↕️ If you love a flight deal, is hosting its biggest sale of the year: 51% off of memberships with code AFFILIATE51. A year of deals for $25.

• 📚 Last month, I interviewed Bookshop.org CEO Andy Hunter, and I’m thrilled to say the company brought in nearly $1.5m in revenue through its Anti-Prime campaign, with $210k going back to support local bookstores. Community over convenience.

• 📖 Speaking of books, if you’re a fan of Silvia Moreno-Garcia’s Mexican Gothic, you’ll devour her latest book, out this week: The Intrigue. SMG is a master of building time and place, and she has done it again—you’ll feel transported to Veracruz, a different kind of trip.

• 🧼 I’ve been testing travel-sized natural deodorants (worn for at least 24 hours after a shower), and I come bearing results:

  • This Each and Every mini-set includes a Coconut and Lime scent that smells like a piña colada (complimentary) and yes, it works.

  • This gender-neutral AKT set features five of their best-selling fragrances (I’m partial to Orange Grove), and I was impressed here as well. The minis are super small though, so keep that in mind.

  • The Salt & Stone aluminum-free deodorants didn’t work as well (I’ll spare you the details, you’re welcome), but the Saffron and Cedar scent is addictive. If you’re not a super sweaty gal like me, you’ll be just fine!

See you next week! —Henah x

The human body is a fickle thing: While in London last fall, I dealt with debilitating jet lag every single day, lying awake all night—only to fall asleep around 7AM until noon. On my recent excursion across Europe last month though, I didn’t have a single issue and fell right into the Circadian rhythm of Central European time-zone. I returned home and immediately adjusted back to EST.

When we talk about slow, quiet travel—trips that allow you to rest—we can’t ignore the importance of quality sleep. We of course need it in order to function, but we’re often willing to forgo it when there are special experiences on the line or when FOMO strikes: a sunrise hike, a late-night party, getting drinks with friends.

Travel worsens our ability to recover, especially when we’re crossing multiple time zones and traveling east, which means advancing our internal clock. That doesn’t just mean sacrificing sleep or dealing with fatigue; it also affects our entirely body, including indigestion, weakened immune function, and reduced mental performance.

With one parent who suffers from sleep apnea and the other from insomnia, I have long known sleep issues are likely to affect me. So last November after my experience in the UK, I began experimenting with different tools and techniques—in addition to the rituals I’ve honed over the last decade—to fight jet lag, enjoy quality sleep, and actually feel rested.

A few caveats: I’m admittedly a night owl (or the wolf chronotype), I aim for eight hours or more a night, and I’m a huge fan of naps. And as someone with a few chronic disabilities, I am what I’d call a 1% Sleep Spender: I will happily invest in sources to improve my sleep, period.

However, these are only the tools that have worked for me over the last eight months of testing. I am not a licensed professional, so please do your own due diligence and check with a medical professional if you consider any supplements. I’ve broken down the different stages of preparing to fight jet lag from before you leave to readjusting upon your return. (And if you’re curious how jet lag works to begin with, this primer breaks it down well.) Sweet dreams!

The Key to Quality Sleep While Traveling Starts Before You Leave

The easiest way to signal that you’re ready for bed to your body will be following the same rituals you would back home. In that sense, how you sleep at home is highly instrumental in a new location.

Amy Behimer, a Pharm.D and board-certified health and wellness coach, also recommends “trusting in the tiny” habits to create consistency while on the road: “Bring micro-versions of your usual bedtime rituals so your brain knows it’s time to rest, even in a new setting. That might mean jotting a single line in a journal, reading a few pages of a book, applying a familiar hand lotion, or listening to one calming song you play before bed. Pair these with tiny environmental shifts—like dimming your phone screen to match your destination’s nighttime or slipping on cozy socks—and you’re giving your body repeated cues to downshift into sleep mode.”

My bedtime routine is fairly simple and reliable: My husband and I get ready for bed, and then play the NYT games together on my phone. By the time I get to the crossword, he’s already fallen asleep, and once I’m done with the crossword, I’m ready to knock out, too. If I’m not particularly sleepy, I’ll start reading a book, and am typically asleep in 20 minutes.

But in some seasons of life, I have a harder time falling and staying asleep. After many years, this is the “survival tool kit” I’ve built in desperation to get some ZZZs:

• I always thought a cooling mattress might be overhyped, but as someone who has a hard time with hormonal thermoregulation, investing in one truly changed everything for me. This is what we’ve had for several years—at one point recently, our cat punctured the pad and we would’ve paid happily for a replacement despite the very high cost, because we love it that much. My husband sleeps cooler than I do, but I find that a schedule between 75–85 degrees helps me stay comfortable all night long.

• Loose clothing and soft, cool sheets are key. As part of my past work, I tested out extremely expensive linen sheets (skip, they don’t hold up in the wash) along with cheap big-box stores. I’m surprised to say it, but I do find Target’s Essentials sheets (pre-cancellation) to be a solid budget pick, and I like Miracle Made for higher-end crisp sheets because they’re also anti-microbial and cooling.

• I store this weighted sleep mask next to my bed, and I have a version I’ll also bring on trips with me. When it’s starting to get light outside during a bout of insomnia, I’ll throw this on for immediate relief. Plus, it beats investing in expensive blackout curtains.

• I like these nightly sleep packs—they’re melatonin-free and non-habit forming. They’re expensive, but they do work for me. If I don’t have access to these, I like taking one of these gummies; it’s not enough THC to make me feel out of control, and helps me relax to the point of sleepiness.

• Because of my aforementioned chronotype, my alarm would often go off when I was in the middle of a REM cycle, causing intense grogginess and headaches. I have since shifted to an app called Sleep Cycle, which tracks your sleep stages via your phone’s microphone and wakes you up during the lightest sleep phase. It has been an absolute game-changer. It’s currently free to use all summer! I am also obsessed with tracking my sleep score (I wear my Oura ring religiously) and noting any trends or concerning patterns over time. If you’re curious about how they compare:

Planning Ahead Against Jet Lag

You know you’re going to embark on a trip across multiple time zones, and you have your plan once you get there. But what about in the days leading up to your departure and in transit? You guessed it: That’s just as important.

• First, plan your sleep like you plan your itinerary—far ahead of time, if you can. According to Major Allison Brager, US Army Sleep Specialist, “Banking on sleep prior to anticipated sleep deprivation and jet lag can reduce the consequences of jet lag. Army scientists have conducted studies in the lab and in the field showing this hack is legitimate and works under most circumstances for reducing physical and cognitive fatigue, improving mood, and preserving decision making.”

• Far and away, the #1 app I’ve heard to help manage jet lag is Timeshifter. You put in your flight times, and it’ll auto-create an itinerary to follow to minimize sleep disruption (like avoid caffeine for nine hours, or see bright light for the next three hours). You can set it up before you leave, and it incorporates all stopovers. Your first use with Timeshifter is free, and then charges for future trips.

• If you want something a little more regimented and with some supplemental help, you could also try Flykitt. My husband tested it out on our London trip (I can’t have caffeine) and had a positive experience: The app, in conjunction with supplements and blue-light filtering glasses, gave him a guided itinerary of what to take and when. The downside is remembering to bring the meds with you each day and taking them on time. But if you want to fight both jet lag and bloat, this is a good go-to.

• Nearly every expert I heard from said to pack a basic sleep kit: an eye mask, ear plugs (I like these), or even a calming scent like lavender spray or a perfume that reminds you of home. While most airlines might offer this already on an overnight flight, many won’t, even if it’s a six-hour transatlantic flight during the day. This is worthwhile to bring with you beyond a flight as well, because you never know if a hotel or train will deal with noise or light disturbances.

• On the note of ear plugs, brown noise will mask engine noise while flying, and pink noise can mask road hum and tire noise if you’re driving.

• Never forget a sturdy neck pillow. I also saw this hack—I can’t speak to it myself yet, but in any case, don’t forget proper neck and head support.

• Wear comfortable, loose layers. You don’t want to be tossing and turning in an airplane seat wearing jeans, and I always pack a cardigan, scarf, or outer layer that can act as a blanket.

• Take a 30-minute walk before boarding: Try to tire yourself out as much as you can before getting on the plane. Walk around the lounge, check out duty-free shops, people-watch throughout the terminal, whatever you can do to get those steps in.

• Book seats above the engine or alongside the wings, typically between Row 10 and 25. You’re less likely to get motion sickness, and the hum of the engine will act as white noise.

• Once you board the plane, immediately change the time on your phone to the new destination’s time, a gentle nudge to your body and brain to adapt.

• Longtime readers know I need Dramamine on all flights to avoid motion sickness. I take the non-drowsy version when I’m flying short-haul, but I’ll take a full regular Dramamine if I’m on a 4+ hour flight, and that also helps me stay sleepy enough when I return home to go right back to bed. If I land and I feel groggy somewhere and need to power through, I will chug water until it feels flushed out of my system. I also avoid alcohol on planes, as I know my sleep quality will plummet.

Fight Jet Lag Once You’re There, Beyond “Just Stay Awake”

Look, we’ve all heard it time and time again: Just power through and try to stay awake until your usual bedtime. It works, I get it!

That’s always easier said than done. There is no way I will land at 6AM after a turbulent redeye and stay awake until 11PM—I’m not even up at 6AM at home. In this case, Martin Reed, founder of Insomnia Coach and board-certified health and wellness coach, has some helpful advice: “If you reach your destination at a time when you’d normally be sleeping, you might want to grab a bit of sleep and then try to get up at your normal time…A consistent out of bed time in the morning, a day filled with meaningful activities, and not chasing after sleep (for example, by going to bed earlier than normal) are often the most helpful ways to give sleep the opportunity to get back on track while traveling.”

If you’re really struggling to stay awake, according to Major Brager, you can caffeinate intentionally: Have two strong cups of coffee (200 mg of caffeine) every four hours at least eight hours prior to bedtime, especially if you have a busy day ahead of you. For example, if you aim to sleep at 10PM, you can have coffee at 6AM, 10AM, and 2PM before cutting off. Or, if you make it until the evening, she recommends a small 3mg dose of melatonin the first night or two to help soothe your body.

As for me, I try to strategically time a nap in my day, even if it’s up to two hours long, instead of the oft-suggested 30-minute power nap. If I land at 8AM, I’ll sleep at the hotel from 10:30AM–12:30PM, and then continue on until about 10PM.

The other two most important and evidence-backed ways to support your Circadian clock that you’ve also likely heard before: Timing your light exposure and your meals. Getting bright light first thing in the morning resets your internal clock, and if you schedule all your meals in line with your new destination’s time zone, that will act as an additional signal to your body.

Upon Returning Home

You’ve probably also heard the adage that it takes the body one day per time zone to readjust to its Circadian rhythm. In my experience, I’ve found that to largely be true, so if you can, take an extra day at home for yourself to re-acclimate—an extra paid day off, coming home a night early on a long weekend or holiday, etc. I always worked to maximize my time in any destination but as I get older, I find the value in coming home a night early to decompress and readjust.

As for falling asleep and staying asleep back in your own bed, depending on how much you want to optimize: I’ve tried this Somnee sleep headband. You wear it for 15 minutes before bed, and it’ll send “personalized neurostimulation to your brain’s natural sleep signals,” which helps you fall asleep faster and boosts restorative deep sleep.

It’s a solid sleep gadget, but I often wake up with the Somnee off of my head, so keep that in mind if you move around a lot like me. Somnee is HSA/FSA eligible and you can try it risk-free for 45 days, so if you really struggle, this could be a Hail Mary. Otherwise, it’s back to my tried-and-true routine!

While traveling back (from the east, especially) can be harder on sleep once you’re home, the good news is: Generally speaking, your sleep duration will bounce back quickly. And then it’s back to (hopefully) eight hours in your own bed until your next trip, and there’s no better feeling.

If you have any tips to combat jet lag and get quality sleep, whether at home or while traveling, please do share them—because we could all use more rest and recovery:

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• 🚗 Speaking of insomnia, I will typically read when I can’t fall back asleep, and this recent read about a car crash featuring three teenagers and the parents who might end up in prison was riveting while I laid awake at 4AM last week: “The Oak Grove 100 was an attempt to reach 100 mph on a two-lane road with a speed limit of 35. But in the long aftermath of Sophie’s death, it was possible to see it another way: as a percentage. When the time came for the distribution of guilt, there were 100 percentage points to hand out. Who should get them? How many each?” I’m an AJC subscriber, so sharing a gift link here. (Atlanta Journal-Constitution)

• 🚂 “Before I fell in love with Paris, I fell in love with Eurostar.” A fellow writer from the Southeast waxes poetic about the same train I took from London to Paris last month, and it truly is a form of magic. ()

• 📋 This solo traveler shared her list of non-negotiables when she’s traveling alone. They align well with my own philosophy, and she has other valuable recommendations I’m incorporating.

• 👀 This renowned brand is hiring a Senior Editor focused on travel, up to $125k.

• 🥰 Annie Lachhman-Persaud has cerebral palsy and uses a wheelchair. That doesn’t stop her family from doing daycations around New York City, and documenting their local travel. Heartwarming, family-focused, and hopeful. (Travel + Leisure)

See you next week! —Henah x

Newport, RI is a destination that holds a lot of meaning in my heart, and yet I don’t remember a single thing I did there. Let me back up.

For several years after college, my close girlfriends and I would try to travel to a nearby town around Memorial Day Weekend. In 2019, we chose Newport.

On the day we were supposed to drive over, my best friend, Sarah, and I had lunch plans, and I hoped to get on the road soon after. Well, it turns out that those “lunch plans” were actually…my engagement. Sarah was actually there to photograph our proposal on our apartment’s rooftop overlooking New York City.

After lunch, I left for the City by the Sea. I arrived that weekend with a new ring on my finger and a new-to-me place to celebrate. I remember it vividly as being beautiful but the weekend was, of course, eclipsed by bigger life news, so I couldn’t tell you where to go or what to eat.

Luckily, of the Bad Bitch Book Club, or @mackinstyle as you may know her online, frequents there often. With nearly 100,000 BBBC followers, I’m a huge fan of the community Mackenzie has built and what BBBC is all about.

Mackenzie generously shared all of her tips for the perfect trip to Newport saying, “It is a place with great food, gorgeous ocean views and more activities than you could possibly do in one single weekend. It makes my heart sing. I love it there.”

I think you’ll love this city just a few hours away from New York City and Boston—whether you go for a sunny long weekend, a rainy getaway where you head to a museum, or a Christmas escape, Newport is a gem. Thank you Mackenzie for your invaluable tips, and I’ll let you take it away from here…

Where the Vanderbilts Used to Vacation—And You Can, Too: Newport, Rhode Island

Between 1870 and 1910, Newport rose to prominence as a hot summer destination for America’s wealthiest families. These days, you’re a lot more likely to rub shoulders with the wealthy at a dive bar after a sailing race, but back then, it would have been in a ball gown. (Please note while doing research about this I quite literally stumbled upon something called a “Dog Ball” where Mamie Fish hosted people’s pampered pups for a three-course dinner. Eat the rich, etc, etc.)

Today, Newport is still packed full of people with money, but they tend to leave their ball gowns at home. Instead, you’re a lot more likely to find women in their forties from New England wearing designer white jeans and a cashmere sweater with a glass of Sancerre in their hand and a nice-but-not-too-nice bag on their arm. The vibes are casual (dare I say, truly quiet…) luxury. The weather is 10 degrees cooler than Boston and New York and thus far more enjoyable in the summer.

Where to Stay

• Short-term rentals are actually illegal in Newport! If you’re interested in renting a house, look next-door in Middletown. They have great beaches, it’s only a 15 minute drive from downtown, where Newport Vineyards is located. This one can sleep 10 and is only $500 a night—a truly great deal.

• My absolute favorite hotel in Newport is The Cliffside Inn. It’s a renovated Victorian mansion with beautiful rooms (many with fireplaces), a fabulous cocktail hour for their guests, and the location is right off the famous Cliffwalk. It’s a little out of the way if you’re trying to walk everywhere, so i’d recommend a car unless you plan to Uber.

• If you’re traveling without a car, Hammett’s Hotel is ideal. You’re walking distance from everything, and they have a huge outdoor space overlooking the harbor. It’s super clean and well-appointed, and they tend to have really great off-season rates.

• Ballin’ without a budget? Gardiner House is at the top of my to-stay list. Even if it’s out of your budget for a hotel, they have an incredible cocktail bar you simply must see.

Shocked by the prices in July & August? I insist Newport is better during the shoulder seasons. But if you’re committed to the summer—look at some chain hotels in Middletown (so close, can’t express how close) and use those points!

Where to Eat & Drink:

I am guilty of revisiting the same places over and over again in Newport. Once I’ve discovered something I love, it’s hard for me to deviate from my favorites.

• Thames Street Kitchen: Why would you go all the way to Rhode Island to eat at a steakhouse? For the bonito brown butter sauce on the side. But seriously, this inventive menu (think bone marrow escargot) would be massively viral even in New York City. Which should be your clue to book your reservation a week or two in advance or run the risk of a 9:30pm dinner.

• Clarke Cooke House: Delicious seafood in a warm environment, with the BEST bartenders. Whether you want a classic lobster roll or are in the mood for sushi, you can guarantee they’ll have something fresh and beautiful for you to eat. I absolutely adore this place and recommend the mussels and the tuna tartar.

• The Black Pearl: If you want to sit outside and want to make sure the food you’re eating is worth the real estate premium, The Black Pearl is your best bet. They have an A+ clam chowder, great drinks and the best setup on the wharf. Is it my favorite food on the island? No, but it’s my favorite experience.

• Bar ‘Cino: There is a rumor and absolutely no proof that all three of the (musical) Jonas Brothers once ate here and that is why it’s always so busy. But I think the word has just gotten out that they have the best bolognese sauce in all the land. The food here is warm and comforting, which is why I go back every single time I’m in Newport. (Ed. note: I’m obsessed also with the fact that Bar ‘Cino is 100% employee-owned!)

• One Pelham: The floors are sticky, the cover is $20 cash, but the band is genuinely good and you’re more likely to see people dancing with their friends, instead of scrolling on their phone.

• Pour Judgement: A genuinely excellent dive bar with fair prices, a great staff and a menu that makes you want to skip all the fancy sh*t in Newport just to have a Penne Carbonara large enough to feed a family of four for a week.

• Gardiner House: On a fancier note, I absolutely adore the Studio Bar at Gardiner House. It’s dark and moody and the cocktails are fantastic. This is a must-visit if you’re visiting off season and want to hangout somewhere with a fireplace and a chic ambiance. For something similar, the Vanderbilt Hotel.

• Sweet Berry Farm: If you’re going the rental route, make sure to check out Sweet Berry Farm. They have delicious pre-made snacks and salads and you absolutely cannot skip the homemade strawberry whoopie pies!

• Castle Hill Inn: Nobody (that I know) can afford to stay here—but that doesn’t mean we can’t have an Aperol Spritz with the best view in the North East! Truly a gorgeous experience.

What to Do:

• Charter Books: You know that feeling of excitement you get when you walk into a really good bookstore? That’s how I feel about Charter. Though it’s on the smaller side, they have allllll the buzzy books (usually signed) and are staffed with great conversationalists. They also have a wonderful children’s section. A few doors down you’ll find Closet Revival: it’s a consignment shop that is absolutely worth bopping around.

• Cliff Walk: If you are given a beautiful day in Newport, you must walk at least part of the beautiful 3.5 mile stretch along the seaside known as the Cliff Walk. On one side, you have the Atlantic Ocean, and on the other, the iconic mansions. It’s free and it shouldn’t be skipped (Beware: you can only do part of this with a stroller!!).

• Newport Mansions: As previously mentioned, Newport has historically been a playground for the rich and famous. Nowadays, most of their homes are museums. The Breakers is the most famous and should definitely be your first visit. Also, I know I keep trying to convince you to visit outside of the summer, but please consider this at Christmas time! Gilded Age fans—this is your moment.

• Marble House Tea: Alva Vanderbilt was given this mansion as a gift for her 39th birthday. Imagine. She chose to build a Chinese-inspired tea room right on the edge of a cliff where she hosted members of the suffragette movement. Now you can go have a three course high-tea while dining on “votes for women” plates. Not going to lie, kind of an amazing experience.

• Newport Art Museum: If I see an art museum, I’m going. Newport Art Museum is far from world-renowned, but it is respectable! And it’s in a beautiful old mansion (isn’t everything here?) If you love art, it’s definitely worth spending an hour here.

• Vintage Shops: Folk Vintage, Daydream Vintage, and Nest are all within walking distance to each other and carry a wide range of secondhand and vintage pieces at a great price. For homeware, I’ve found cool stuff at Antique Boutique and Leeside Antiques.

What Else to Know:

Newport is incredibly walkable, and you truly do not need a car (though I always prefer one—sue me!) You can get there by taking a Lyft from the Kingstown Amtrak station (30 min, approximately).

Though summer is very popular, I cannot stress enough how lovely it is during the spring and fall, especially if you hate crowds. That said, Newport is becoming more and more popular to visit, so planning your meals is a great idea.

Also, if you are traveling with kids, my recommendations change ever-so-slightly:

• Skip TSK and opt for Bar’Cino or La Vecina Taqueria next door (both have affordable kid’s menus).

• Visit the aquarium instead of the mansions (unless your child is a walking angel; mine isn’t!).

• Hit Ryan’s Amusements for old fashioned arcade fun (honestly, who needs a kid for this?) And if you like sailing– know that there are virtual activations for them to play with there as well.

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• 🏆 What a joy hearing about your favorite books in last week’s edition. The winner of a $50 gift card to Bookshop.org is… ! Please DM me your preferred email and we’ll get that sent your way.

• 🫠 Thank you to everyone who told me the link for my new favorite shoes didn’t work! I’m resharing them here—with the right URL this time—as they just keep getting better and better.

• 💳 As your resident “credit card perks evangelist,” I’m here to remind you: New quarter/half, newly reset benefits! Don’t sleep on AmEx Platinum’s $300 biannual hotel, $100 dining + $75 lululemon credits (I once again recommend this cropped rain-jacket). For Chase Sapphire Reserve, your $150 Stubhub/Viagogo and $150 dining credits are back. For other premium cards, here’s a handy roundup. (The Points Guy)

• 📚 I was a huge fan of Jessica Knoll’s previous book, Bright Young Women, so I hopped on the chance to read an ARC of her book coming out next Tuesday: Helpless. I want to be clear: It’s extremely dark and controversial, but the twists really turned the plot on its head. If anyone else reads, I’d love to know what you think!

• 🧺 I recently tried these laundry detergent pods and found the scents to be really luxurious and intoxicating. If you worry about your clothes smelling while traveling, I would absolutely get the dryer sheets and throw some into your luggage. (They also have a scent brochure if you want to test them all.)

• ☀️ Much of the world is—or has recently been—in a heat wave; it’s a sweltering 95 degrees here in Atlanta. If you’re traveling, please be safe with these tips from the experts. And if you’re on an SSRI like me, drink 2x as much water. (AFAR)

Have a wonderful holiday weekend if you celebrate—see you next week! —Henah x

When we first launched Departure nearly two years ago, we envisioned covering all the lesser-appreciated parts of travel: The slower mornings, the space to reflect, and the books we brought along for the journey. Because in this author’s humble opinion, books and slow travel go hand-in-hand; they require thoughtfulness, deep attention, and a desire to transport yourself elsewhere.

Over the years, we’ve shared some of our favorite reads (and bookstores)—the ones we buried in sandy bags home from the beach, or the longer sagas we devoured when we weren’t able to travel in the pandemic.

That’s why I’m thrilled to interview Andy Hunter, the CEO behind Bookshop.org, a platform supporting independent bookstores around the country.

Why this week? Well, because it’s one of my most dreaded times of the year: “Prime Day,” which ends on Friday. Instead of highlighting deals for a company I do not use or recommend, I wanted to showcase an organization I do love that wants you to support bookstores, not billionaires.

If you can, please consider diverting your dollars away from Amazon this Prime Day and shopping via Bookshop or any other independent business instead. (They’re offering free shipping, too!)

To sweeten the deal, Bookshop has generously agreed to give one lucky winner a $50 gift card. 💕 In order to enter, you must “like” and comment on this post sharing your favorite book. US or UK entrants only, winner to be announced next Thursday.

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An Interview with Bookshop CEO, Andy Hunter

Andy, you launched Bookshop.org as a more ethical alternative to Amazon. Longtime readers know I am very vocally anti-Amazon, and I’ve been a staunch supporter of Bookshop for years, so thank you for being here. At a base level, tell us what Bookshop is, your approach to supporting independent bookstores, and the impact you’ve created.

I had the idea for Bookshop as I knew more and more book shopping was happening online, and almost all of it was going to Amazon. Most people and publications who posted about books were linking to Amazon back in 2000–2019. We needed an alternative bookstore that we could link to that would support indie bookstores, and we needed to make it easier for bookstores to sell online so they could fight back against Amazon.

I was met with a lot of skepticism at first, but once we launched (in January 2020), it quickly became clear that there were lots of people out there who didn’t want Amazon to have a monopoly on bookselling, and who wanted to live in a future that included local, independent bookstores.

Since 2020, independent bookstores have boomed, and we’re really happy to have been a part of the renaissance. To date, more than $47 million has been donated back to local independent shops.

It’s funny, as a kid, my mom would always tell me to stop buying books at the Scholastic Book Fair, and to borrow them instead. But my father would say, “If books are the one thing she wants to invest in, let her.” Now, my husband and I have built our own library to honor these physical books. Bookshop launched during the pandemic, and books became a lifeline for a lot of people—their way of escaping to another place when they physically couldn’t. Do you think that moment changed why people buy books?

I think the pandemic did not change why people buy books; it just made the reasons we read—like escaping from our day-to-day lives, increasing understanding, and connecting to other humans—more important. People had more time on their hands and were searching both for distractions and answers, both of which a good book will provide.

What was unexpected was how the pandemic motivated people to support and protect their local bookstores. Though we had been through twenty years of the slow decline of independent bookselling, when we were suddenly faced with the consequences of losing them to lockdowns, we rallied behind them.

That was incredible to see, and it looks now like a lasting shift in reader behavior: Over 1,000 new bookstores have opened since Covid, and last year, 75% grew year-over-year.

I have a “tradition” I live by: For every new bookstore I go to, I allow myself to buy a book. It’s a wonderful way to build up my library, but also to remember the place—and my experience—at that moment in time. I’ve collected books on trips to Greece, China, Colombia, Uganda, and so on. You’ve spoken before how, as a child, you’d seek out new bookstores when you went on family vacations. Do you still hold that tradition today? Do you have others you try to follow?

Absolutely, though I am too bashful to introduce myself most of the time. I was just up in the Catskills and visited the incredible Golden Notebook in Woodstock. I will be in Maine later in the summer and look forward to visiting The Briar Patch in Bangor and Hidden Barn in Bar Harbor.

As you’ve noted, more than a thousand indie bookstores have opened over the last few years, particularly as the importance of third spaces and community-building has grown. When you talk to bookshop owners, how are they feeling about this momentum? It’s no surprise that Amazon still reigns supreme, but it feels like (finally!) the tides are turning a bit more.

New indie bookstore owners are really excited and passionate about the momentum and popular support for indie bookselling. Older veterans are more wary, because they know that margins are still low, and we might be one economic downturn away from reversing some of that progress.

That’s why everyone at Bookshop is now obsessed with growing and taking more of Amazon’s market share, bringing new revenue streams like ebooks to indie bookstores, solving more bookseller tech and data problems, and generally doing more to make bookselling more sustainable.

Booksellers are proud of what they’ve accomplished and happy with how things are going, but we’ve still got work to do to make sure the renaissance of human, local, indie bookselling continues.

This is, at its core, a travel newsletter. Tell me about some of the indie bookstores you’d love readers to frequent, or the ones that have stayed with you for years and are worth traveling to.

Well, there are too many and I'm not sure I should play favorites. But one favorite is Word on the Water which is on a barge in a canal in London.

Ed. note: I was actually just here which I mentioned in last week’s edition! Here’s a photo I snapped on-board:

Continuing on the theme of slow travel: Indie bookstores are described as one of the last frontiers of “unhurried spaces.” There isn’t an AI-based algorithm, next-day shipping, or even a sense of urgency in a bookstore: You can spend a full afternoon immersed in a book there and you look to store clerks as expert curators. What do you think it is about a great indie bookstore that makes people want to stay? (As someone who hopes to own my own secondhand bookstore and community space one day—like every other millennial woman in the world—I am eager to hear!)

A great indie bookstore enlivens the senses: the sight of the book piles and shelves of undiscovered stories, the smell of fresh new books or musty used books, the feel of their covers and pages... Just thinking about it makes me want to run to one right away.

The other wonderful thing is that they are filled with other readers, kindred spirits, and booksellers who have devoted their careers to helping people like us discover the books that will move us, change our lives, entertain us, or all three.

I’m always interested in ways we can explore a local culture that isn't a tourist attraction or just checking off a Top 10 list from TikTok. Bookstores can tell you so much about a neighborhood or a moment in time—I’m thinking of Rough Draft up in Hudson Valley, or Baldwin & Co. Books in New Orleans. Is there a bookstore you've visited where the curation itself felt like an education, or that it was an experience that moved you?

I think all good indie bookstores educate and move readers. Shelf-talkers and handsells are amazing ways to discover new books, far better than any algorithm–and I love the delightful way that booksellers can call attention to subgenres, like Walden Pond Books in California curating "microhistories" which are nonfiction with an intense concentration on a single subject like the history of tea.

I’m going to rapid-fire a few questions I’d love your recommendations on. Give me the first suggestion that comes to mind:

• A book that changed your life.

  • The Autobiography of Malcolm X completely opened up my young white suburban mind when I encountered it while on vacation in a cabin at sixteen years old.

• The most innovative or original initiative you’ve seen at an indie bookshop.

  • I once went into a bookstore that had a display of books called "Shade-Tippin'": all mysteries and romances featuring women tipping down their sunglasses to make eye contact with the reader. (Think titles like Counterfeit, A Love Catastrophe, and Heist Society.) Unfortunately, I forgot which store! But I love humorous and surprising curation like that; Amazon would never.

• A book that will emotionally ruin you, but that you consider mandatory reading.

  • Well, for me personally, probably Bridge To Terabithia which ruined me, age eleven. More recently, I ruined my daughters by reading them Charlotte's Web. I apologize that these are such normal, required reading picks! ​

• The most remote bookstore you know of.

  • I love to use Bookshop.org's bookstore finder to find out-of-the-way bookstores, which is how I found The Islander bookshop in Kodiak, Alaska. However, I am sure there are even more remote bookstores, and I'd love to hear about them!

• A book you read to escape.

  • I had a blast reading Lightning Rods by Helen DeWitt, though it's also disturbing. I guess I don't really read to escape, honestly. But I love when a book makes me laugh.

What’s next for Bookshop, or maybe more broadly, where do you see independent bookstores going from here? We're seeing many bookstores become genuine travel destinations in their own right, with their own cafés, events, and residencies. Do you think that's the direction the movement is heading?

I think humanity has a kind-of collective immune system, and in the age of AI, social media depression, and atomization, we are re-discovering the importance of community spaces, shared culture, and personal connection, which bookstores offer so much of. I am so happy that there is a bookstore boom going on right now, one that no one expected a decade ago. It gives me hope.

I think we’re going to see more bookstores as creative spaces that cater to vibrant subcultures like romantasy readers, cookbook lovers, or alien-life believers, and that’s great. People need connection; books connect us with ourselves and our history, and bookstores can connect us with fellow readers, authors, and neighbors.

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• 👡 Plantar fasciitis means I often have to sacrifice style for comfort, but I was truly floored at how comfortable (and chic) these shoes were right out of the box—to the point where I’m going to wear them in Europe next month repeatedly. They’re splurge-y but have been worth every penny, and they’re thin enough to pack!

• 🍽️ Last chance to use your dining credits for the quarter: $150 to OpenTable with the Chase Sapphire Reserve every six months, $100 to Resy from the AmEx Platinum quarterly. Bon appétit!

• 🏕️ The trend of “gramping”—or the concept where grandparents and grandchildren go camping together—is so wholesome. One grandfather said, “It’s put a new lease of life back into me that I wouldn’t have had if I’d have been spending the time back home on my own.” (Nice News)

• 🗺️ Want to meet up with a friend somewhere around the globe but don’t know the optimal place? (Read also: Bachelorette parties.) This handy app, Midway Travel, will help you figure it out, complete with non-stop flight options and midway point data. I tested it out between Atlanta and where my best friend lives in Seattle, and looks like we have an excuse to head to Denver.

• 🤯 These “sea nomads” have lived at sea for 1,000 years in Malaysian Borneo, moving and rebuilding their homes on the water as they track fish. They rarely step foot on land. (BBC)

See you all next week, and happy (almost) July! —Henah x

This edition is available to all subscribers, courtesy of our sponsor Sky Key.

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At the start of 2026, I gave myself a challenge: To go on a solo 10-day international trip. I’ve traveled solo many a time, but I hadn’t done a multi-country trip in years, and I wanted to push myself out of my comfort zone.

I booked ten days landing first in Rome and leaving from Paris, giving myself the freedom to do whatever I wanted in between. I intentionally chose three cities I’d visited before, so I could feel as comfortable as possible, and it removed any pressure to see the sights," instead opting for a slower pace.

(If you’re curious about how I planned to stay safe, I’ve shared some tips on this podcast and in this previous post.)

Two days ago, I returned home from my trip. How did it go, and what did I do? I’m sharing exact numbers and plans below, as well as lessons I learned along the way, so you don’t make the same mistakes I did.

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Stop #1: Italy

A question I am often asked is how I can afford to travel regularly, and in this case, to Europe during peak summer. The answer, again and again: Points.

Back in January, I used the PointsYeah Daydream Explorer function to play around with dates and cities (which I recapped here). I knew I wanted to spend the first half of this trip in Italy, so I booked a flight on Flying Blue from ATL-MAD-FCO for 36,000 points and $48.10 in taxes.

In retrospect, I probably would’ve booked the direct flight instead of the one with the layover, but I had used a lot of points lately and was worried about losing them all, so I kept this as low as possible.

I landed at 3PM at Fiumicino Airport, and for reasons unknown, I decided to take the train into the city—maybe because it was 1/4 the price for the same travel time, or maybe because I wanted to get comfortable with the train, as I’d use it the next day.

It took longer than I intended (the first train left without me, fun!) and it wasn’t fun to carry my bags from Termini to my Airbnb, but alas, I learned my lesson.

The following morning, I doubled back to Termini for my train to Grosseto. While you can purchase tickets at the station, I highly recommend downloading the Trenitalia app and buying them in-app. The ticket was approximately 20 Euros.

By the time the track number appeared, it was the farthest track in the entire station, nestled all the way in the back—a half-mile walk (!). Many of us booked it to board the train on time, and because it was particularly crowded that morning, you could not comfortably sit with your luggage.

My lesson here? Start walking as soon as your track number shows up, and be prepared to stand on the train if you have to, even if it’s a 2-hour ride.

Eventually, we pulled into the Grosseto train station and I took a cab from the station to my favorite hotel in the world. The last time we went here, my husband and I had rented a car, so this was a new experience, and it cost 50 Euros to get there from the station despite being only a 20-minute drive.

For when I inevitably return, I’ll probably save myself all of the aforementioned hassle and just book a car again. I’m really glad (and proud!) I used public transit, but I’m not entirely sure I saved any money or time.

I arrived at La Pescaia, and finally could breathe. It was like coming home.

I was booked from Sunday to Thursday, and looked forward to finally sleeping in, eating nourishing and delicious meals, and lounging by a pool for hours on end. As the time before, it did not disappoint.

I’ve waxed poetic before on how magical this space is, closer to the west coast of Italy, outside of Porto Ercole. There are a limited number of rooms, and the property is expansive enough that it never feels busy or crowded. It was exceptionally quiet during the time I went, where some days, I saw maybe two or three other parties and no one else.

Their food is impeccable—elevated peasant dishes (zucchini carpaccio with crushed pistachios and lemon olive oil, pappa al pomodoro with old bread)—the wine list is excellent, and the portions are generous even by the pool. And at $275/night, it is, in my opinion, a steal for a Tuscan-style summer. If I could, I would book years in advance.

Having that much downtime gave my brain a break, but it also led me to several realizations that are personal and vulnerable, but worth sharing:

• Several readers, followers, and people in real life asked why I was doing a solo vacation. Perhaps because they thought I was separating from my spouse and celebrating in an Eat, Pray, Love way? That isn’t true at all—my husband simply didn’t have the PTO, and I wanted to challenge myself to do it on my own. Every night at dinner, when I pulled up to a table for one and spent the time reading a book on my phone, I got stares. I realized I was being judged or maybe even pitied, and that made me even more insecure about being alone. Then my brain thought: Are you projecting your own insecurity about it, and no one really cares? Who’s to say, but it certainly felt like a recurring theme.

• As a short and curvy South Asian woman, I felt distinctly out of place at times: By the pool or eating gelato, for example. In a continent defined by Eurocentric beauty standards, I could feel the judgement from others for daring to get dessert each night or by showing my un-thin body in any way. The thought occurred to me that maybe I was projecting my own insecurity once again, and I tried to quiet those voices.

• I knew that having that much alone time would lead to some spiraling, as my brain tends to ruminate. After a very tough last year, I was worried about letting my brain run loose, and at one point, I did have a very human breakdown. I actually ended up grabbing old papers from my backpack and using it to journal through my feelings, and after calling my husband who gently consoled me, I felt much more at peace. I even texted about it, and she said something that really stayed with me: “Well, I’m even more proud of you for going, then. I’m of the belief that putting yourself in a position like this (where you know a freak out is likely) is one of the best ways to work through whatever that feeling is.” Giving myself grace after such a year was truly the most important part of this trip.

By Thursday morning, I wasn’t exactly ready to leave what I consider paradise, but I accepted my reality. Because I had a very early morning train for Pisa Airport, I had to book a taxi through the hotel, and this cost me 80 Euros (!!).

And when I got to the train station, the most Italian thing to happen did: My train to Pisa was cancelled due to a strike. I panic-decided to jump on whatever train was still scheduled that got me closer to Pisa. (This ticket from Grosseto to Pisa was approximately 15 Euros.) I ended up taking the train to Livorno, transferring to Pisa Centrale, and then transferring again on the Pisamover to the airport.

Once again, I recommend just renting the damn car and avoiding the headache completely. (For the record, I support workers striking for better wages and conditions and would love to be Team Public Transit 100% of the Time, but when you have limited days, a car is undoubtedly a game-changer.)

At Pisa, I dropped off my bags, went through security, and tried to get a bite to eat. It’s a very small airport, so you don’t need to show up three hours early, like in the states. But there are also immigration and customs to go through if heading to another country, so keep that in mind.

Stop #2: London

I landed in Heathrow Airport around 2PM, and after grabbing my bags, I took the tube to The Grafton Arms Pub and Rooms. My coworker-turned-friend Lea and I chose to stay here due to its proximity to Wembley Stadium and its location in Marylebone—a neighborhood I hadn’t stayed in on my five previous trips to the UK. (It is a very cozy, diverse, and boutique-lined area; worth checking out.)

The room was well-kept, clean, and the crew kept small snacks and waters for us, but be warned that it is up several flights of stairs without an elevator. Luckily, their team brought our bags up and down. We walked to a local branch of Rosa’s Thai, had an early delicious dinner, and I went back to rest after a long chaotic day of travel.

The next morning was Lea’s birthday (!), so we celebrated in style: We grabbed brunch at Joon Cafe (get the saffron latte and thank me later), then walked across the city to check out Word on the Water, a bookshop on a boat in the Regent’s Canal. Afterwards, we sat by the barge and made our way to another fan-favorite bookstore: Daunt in Marylebone, which is just a few minutes away from the Baker Street stop. I bought a journal, tote, and a book, and we moseyed along the street stopping in small shops along the way before heading back to our room.

Then it was time for the purpose of my London pitstop: To see Harry Styles and Shania Twain in concert at Wembley Stadium. We managed to get tickets for his first night of twelve there, and after the fact, I made a “trial reel” of what to know about the show that I posted without thinking, and now it has over 120,000 views (lol). The people want to know about what to expect!

(TL;DR: Show up early, public transit is wildly busy, food inside is slim pickings, and the show runs 45 minutes for Shania and two hours for Harry.)

Stop #3: Paris

Then it was time for my final stop: Pareé. I only picked here because the flight to get home from Paris was the cheapest points-wise than any other European hub, and so it was a helpful reminder that, while Paris is gorgeous, it is not the city for me—Rome is and always will be.

I wanted to try something different this time: Instead of flying, I opted to take the Eurostar train from London’s St. Pancras to Gare du Nord.

A couple of learnings here:

• You can compare times and prices on Trainline but I recommend booking directly.

• Book early. When I first looked it up, tickets were around $100, but by the time I went to book a week in advance, it jumped up to $300. I didn’t expect that, but the train was fully packed, so there’s definitely demand.

• St. Pancras station doesn’t have a ton of seating after you pass security and border control. Be prepared to stand while you wait for platform information.

• The train Wi-Fi isn’t reliable—it didn’t work at all during the 2.5-hour journey.

I do think it’s worth taking again; it brings you directly into downtowns in both directions, instead of the airports outside of the city. Plus, the train was clean, efficient, and on-time.

In Paris, I stayed at the NH Paris Ópera Faubourg, about a 15-minute walk from the station. It’s in a safe and walkable area, and I was able to use my Chase Sapphire Reserve travel credit towards this stay, so two nights here only ran me $250.

Upon arriving, I walked around the 9th Arr. to get my bearings, and I ended up in the Passage des Panoramas, which was one of the first covered passages in the city and founded in 1799. Today, it has beautifully ornate architecture and plenty of vintage and antique stores; I purchased old books and prints to bring home. I stopped at Ravioli Nord-Est for some dumpling soup (delicious, cheap) and then headed back to my room.

The next morning, I grabbed an incredible vanilla pecan tarte from Rose Bakery and walked two minutes to the Cadet bus station. I downloaded the Bonjour RATP app and purchased my ticket there, which you then validate on the ride, and I took the bus about 30 minutes north to the Saint Ouen market.

My friend Tyler and I went shopping for antiques here last year, but it turns out, we barely touched the surface at the time. This sprawling market—the largest in the world—was buzzing, with maze-like setups and blocks and blocks of stands. I purchased an artist palette I’ve been wanting for a long time and two vintage pieces of art that I’ll frame for our living room, spending several hours here before my feet hurt too much to continue.

If you like art, books, or design in any way: You must go.

After resting for a bit, I had one last evening to enjoy, so I leisurely strolled around the Montmartre neighborhood again, popping into boutiques, and stopping at Pepe Martyrs, one of the most highly-rated spots for pizza in Paris. It wasn’t anything to write home about if I’m being honest, but it was satisfying enough. Then I moseyed back to the hotel and packed for my return home.

Upon checking in for my flight back to Atlanta, I received an offer to upgrade to Air France business class for $600. I’ve never gotten one before that was cheap enough, but for a lie-flat business class seat for 9.5 hours, I leapt at the chance.

Let me tell you, after 10 days of walking thousands of steps and hauling my luggage, both my plantar fasciitis and hidradenitis suppurativa were acting up, so this was honestly one of the best decisions of my trip and worth every penny.

My original flight was only 19,000 points and $240 in taxes, so once I added this in, I ultimately paid 19,000 points and $840 for business class—not bad at all. Plus, since I get 4x points on the CSR, I gained 3,500 of those points back immediately.

In total, over the ten days, I spent:

• ~57,000 points and $888 on my flights there and back

• ~$700 for trains, planes, cabs

• ~$1,900 on accommodations

• ~$1,000 on food, shops, and miscellaneous

When I add it up, it’s a bit jarring, but I also intentionally paid more for places that were safer, and I had to pay the singles tax on my hotel rooms/Airbnb. Luckily, I budgeted at least $3,000 for this trip earlier this year. The additional spend I racked up between shopping and the business class upgrade, I offset through freelance work.

Five years ago, I only dreamed of a life like this—where I could book this kind of travel for myself and not worry about money. To shop for antiques in Paris, to sip mocktails by a pool in Tuscany, to see one of my favorite artists in his home city.

Maybe most importantly, I genuinely pushed myself out of my comfort zone and it stretched me in ways I couldn’t have imagined a few years back. It reminded me that I can traverse the globe on my own; that I can navigate challenges in other languages and still survive just fine; that even when my brain spirals, I can come back to myself.

I have much to be proud of, and I am. I hope if you decide to do this on your own, that you beam with pride for yourself.

Leave a comment

• 🧳 For this trip, I brought my trusty carry-on along with the BÉIS travel duffle, because it was easier to have two smaller bags stacked atop one another than to roll a massive suitcase on cobblestone streets. I was honestly really impressed by how much this duffle could pack, and it slid onto my carry-on handle so I didn’t have to carry it. (I used the crossbody strap once I checked my bag in.) It looks like BÉIS is offering free personalizations for a limited time, so it might be worth gifting for yourself, as a Father’s Day present, or for the friend constantly on business trips.

• 📘 If you’re a fan of Tom Lake or Bel Canto, I think you’ll adore Ann Patchett’s latest book, Whistler, like I did, as I devoured this in one day while sitting by the resort pool. In the simplest terms, the story is about the impermanence of life, and as someone whose life looks extremely different than it did a year ago, that really struck a chord with me. As with all of Patchett’s books, you’ll be left in awe.

• 🔋 At a corporate event, I was given a portable power bank as swag, and I brought it along with me—now I’ll never travel without it. While the version I have isn’t available, I found this very similar alternative: A 5-in-1 travel charger that includes USB-A and USB-C ports, two charging wires, three travel adapter prongs, and a MagSafe Apple Watch charging pad. I used it every single day, and it became the real MVP of the trip.

• 🥲 If you’ve been following any World Cup content, you might’ve seen Freddy, the German tourist visiting the states for the first time and documenting his trip. He’s become a bit of a viral sensation, and he’s even getting warm welcomes from states like Louisiana. Very wholesome.

• 💳 For AmEx Platinum users: Don’t forget to use your $50 Saks credit before June 30th or it’s gone forever. Maybe for some beauty travel-sized items?

See you next week! —Henah x

Greetings from Tuscany! 🇮🇹 I’m currently on my long-awaited solo trip across Europe, and it’s been both a liberating and interesting experience—it seems people are surprised that a (happily) married woman would travel alone for fun, but I wanted to challenge myself outside of my comfort zone this year, so here we are.

If you’re not sure how to ease into your first solo trip yourself, my older walkthrough might be helpful—plus, the benefits of solo travel are many. It’s worth trying at least once.

Subbing in for me this week is our second guest guide from of . She was one of the first readers to reach out when I first announced these, and I’m thrilled she created this guide to a city I’ve never visited before, but now feel like I can drive to in the coming months to experience. (And of course, if you’re interested in writing a guest guide for Departure, DM me.)

Take it away, Kylah!

Southern Comfort Meets Royal Soul: A Local’s Guide to the Queen City

Charlotte is one of those cities that you need to visit to understand. It’s not a major city, but its mid-level size carries a comfortable balance of “city” remnants, while maintaining its suburban feel.

Charlotte isn’t a tourist city, in my opinion: Charlotte’s best qualities are in its simplicity. You’re not taking a tour bus around Uptown (it’s not downtown, it’s Uptown!). We don’t have many flashy landmarks. Uptown is small in comparison to other city’s “downtown” areas. And though the city is a bit fragmented, there’s not one central hotspot. There’s many—and a different vibe for everyone.

These are all just a few reasons why I love Charlotte. There’s something in the city’s atmosphere that feels like a place people actually live, which is why it’s perfect for slow, quiet travel. If you don’t already know someone who lives in the city, it can be difficult to find the things to do. And now you have me to share a guide on what’s what and where to go if you ever find yourself landing in the Queen City.

You can find me at double booked, again for more travel and lifestyle content, and message me privately here for any further questions!

What to Know

Charlotte’s weather nicely balances all four seasons with a humid subtropical climate that often characterizes the southeastern US. That means hot, humid summers and chilly-to-mild winters with the occasional snow day that shuts down the city entirely. The city boasts beautiful nature, with close proximity to forests, beaches, lakes, parks, greenways, mountains. And not to mention, the sports and entertainment that received a major boost around the early 2010s with the Carolina Panthers’ long-awaited success, the Bobcats officially rebranding to the Hornets, and the welcoming of the new, shiny ballpark in Uptown.

Today, Charlotte is known as one of the fastest growing cities in the U.S. It’s grown nearly 30% since 2011 and is approaching one million residents. And it shows.

Every city has its pains with outsiders moving in and changing the fabric of the city. Despite this, every time I return, I feel the local warmth and charm of the city (and residents) that shaped me. And it’s still beautiful in all its glory.

Where to Stay

JW Marriott Charlotte is my personal hotel recommendation. Centrally located in the city, it has a great rooftop bar with incredible views called Aura.

If I was visiting Charlotte and didn’t want to stay at a hotel, I’d likely opt for Airbnb within these neighborhoods: South End, NoDa, Uptown Charlotte. Here are some recommendations (note: these links are subject to break!):

• This charming guesthouse in NoDa is a charming, design-forward favorite.

• This Uptown apartment is a chic, industrial comfort.

• This home in South End offers proximity to popular bars and entertainment.

Where to Eat & Drink

Charlotte has a diamond in the rough kind-of food scene….allow me to explain. There are quite a few misses, lots of chain restaurants, and no shortage of fast food. That said, the great options are truly great.

favorite reservations.

• Bird Pizzeria. Best pizza in the city. Try a last minute reservation or book two weeks out on Resy. Reservations go quickly! Read about my experience here.

• The Cellar at Duckworth. A speakeasy vibe that’s perfect for appetizers, small plates and cocktails before a concert or show in the Uptown area.

• Church & Union. Ideal for a group dinner/brunch. I recommend the Chicken Karaage and Pei Mussels!

• Sanctuary Bistro serves vegan and gluten-free American fare with a passionate purpose. Elevated and organic, yet simple.

favorite local spots.

• Folia. Great DJs, adjacent to other bars (that often skew 20s crowd) and a delicious lemon drop martini!

• Lottie’s Cafe. This Uptown café, located near the former Epicenter (rip), has the absolute cutest menu with amazing community events throughout the year.

• Night Swim Coffee. Another lovely cafe with several locations, regular community events and a must-experience DJ set on Saturday mornings at the Brevard location.

• Free Range Brewing. I’d be remiss not to mention a brewery, given how the local beer culture has exploded in recent years. This one hosts great events, everything from figure drawing to tango classes, in addition to a cold glass.

places that remind me of my childhood.

• Pelicans SnoBalls. New Orleans-style shaved ice. So fun, so many flavors (over 100!), so family-friendly!

• Rico’s Acai. Fresh fruit, açai bowls, family-owned by brothers from Puerto Rico.

• Tupelo Honey. I live for a nostalgic chain restaurant. Visit the Uptown location for a yummy, filling brunch.

  

What to Do

Charlotte boasts a bunch of outdoor festivals and activities that range from cultural celebrations to family-friendly foodie events. Type in “Festivals This Weekend in Charlotte” on Google and you’re sure to find a plethora of free/low-cost events across the city’s parks and streets. For me, I’m an “arts, culture, activity” lover.

favorite arts & culture.

• Harvey B. Gantt Center for African-American Arts + Culture, Bechtler Museum of Modern Art, and Mint Museum sit adjacent to one another in Uptown. All three museums participate in Wednesday Night Live, including free admission from 5–9 PM every Wednesday. But the admission fees across all three are reasonable.

• Belk Theater is for theatre, art and music performances. Beautiful interior and a large variety for those into performing arts.

• Catch your favorite artist at Bank of America Stadium, Spectrum Center, or one of the countless concert venues throughout the metro area, including the four major outdoor amphitheatres.

favorite adventure.

• U.S. National Whitewater Center: if you love nature, outdoor sports, you’ll love this place. Home to the world’s largest manmade whitewater river, they have outdoor sports all year long, and my personal favorite, ziplining.

hidden gems.

• Mo’ Betta Thursdays. Jazz fans, you have to make it to Mo Betta Thursdays. With a live band playing every Thursday, it’s the best occasion for date night or solo activity.

• Lorem Ipsum Bar. A quaint listening bar with the sole goal of creating a space that provides a sensory experience. This spot hosts everything from Bring Your Own Vinyl events to a wine club.

Any Last Tips?

• Prepare to rent a car or Uber most places. Public transit exists; however, the light rail and buses are limited and slower methods of transportation. You may end up in front of a random subdivision if you take the bus…just saying.

• Asheville and Raleigh are 2–2.5 hour road trips (in opposite directions). The Blue Ridge Mountains are gorgeous near Asheville, and both cities have excellent food options that are a short drive away.

• 🥰 I always pack a travel spray from this brand when I travel. After my husband and I ran out last month, we re-upped our scents (Sunlit Blooms, Xtra Milk, and Fragrance 02), and I brought Sunlit Blooms along with me to Europe. We also use their detergent and room sprays in the scent Taunt, and it’s absolutely the best. (Don’t take it just from me; I turned onto these and she’d agree too!) They kindly gave us a code: Use HENAH15 for 15% off your purchase.

• 💳 AmEx is expanding benefits for Platinum Card holders to justify the $895 fee, and I’m not a huge lounge girlie, but it might be worth checking out for yourself. One lounge is slated to open next year in…Charlotte! Apropos.

• 🎸 How Dolly Parton—America’s longest-running sweetheart—built the tourism empire of her dreams. (WSJ)

• 🌆 , who we met in Colombia when he was solo traveling, recently wrote a thought-provoking post about the transience of cities: “When I read about the past, I’m confronted with a long list of forgotten or ‘dead’ places. Ugarit, Angkor, Harappa, and Cahokia likely don’t ring a bell for most humans today, but for centuries (even millennia) of human life, they were The City of their locales.”

• 👀 Announcing the first-ever partnership between a global airline and hotel loyalty program, oneworld and Taj InnerCircle are joining together to offer members savings and tier-based benefits. I’m not much of a oneworld loyalist, but if you’re a frequent flier of Alaska/Hawaiian, American, British Airways, etc., it could be worthwhile.

See y’all next week! —Henah x

This edition is available to all subscribers, courtesy of our sponsor Sky Key.

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If you’re planning a big trip and unsure about the “best” time to book your most expensive flights, there’s no reason not to try Sky Key—it’s free until it saves you money (25% charge of savings amount) and you always come out ahead. To date, I’ve already saved nearly $600, and our community has saved tens of thousands of dollars.

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Last October, tucked away in the secluded and hilly Yellow Creek Mountains, two of my closest friends in Atlanta, Emily and Michael stopped upon Lookout Rock. Michael knelt down on one knee and proposed with a stunning six-pronged sapphire ring.

Thus began the planning of the biggest event of their lives: Their wedding honeymoon. (I kid.)

Emily and I have been friends for several years, growing closer due to our shared love of travel writing. I’ve shared her work here before—it’s excellent. But what you mostly need to know is that Emily spent several years living in a van (the ultimate form of slow travel) visiting national parks by the time she met Michael, who was working on his PhD.

It’s been such a joy having a front row seat as they plan their wedding. Emily’s come over to decide on decor and florals, I’ve seen her dress (classic and gorgeous, as you’d imagine), and then she came to me with the most important question you could ask of someone like me: Could you help me plan my honeymoon?

Of course, my answer was yes. Ever the Substackers, we thought it’d be fun to give you a sneak peek of the process:

• How do you plan one of the biggest trips of your life, particularly when one half of the couple is Type A and the other is Type B?

• How do you balance the logistics with your vision, along with the pressure to make your honeymoon the best trip?

• How do you know where to invest your limited resources, like money and time? Even if you want to embody slow travel, how do you do that while wanting to “see it all” and knowing you can’t?

So, we’re doing a co-published piece today—both from a tactical perspective if you’re ever thinking about how to plan your own Bucket List-level trip as well as the actual itinerary they landed on.

Ask The Necessary Questions & Groundwork

To get started, I asked Emily and Michael (together and in person) basic but crucially important questions:

Tell me about your ideal destinations and what you want your honeymoon to look like.

I’d gotten the advice from a few friends to plan a “dream trip” honeymoon, something that might be harder to do as the years go by. Our first trip together was to Rocky Mountain National Park, so I thought a beautiful way to honor our next adventure would be to visit a more remote national park. And since we normally plan trips around America, it felt like a good excuse to splurge for something international. Go big, right?

My first thought was the US Virgin Islands, but when a friend reminded me that we could get there fairly easily, I turned my sights to the farthest-rung park I could find: American Samoa. From there, the idea snowballed like this: Well, if we’re going all of the way there, why not also visit Samoa? Why not also visit a national park in another country? It’s relatively close, why not New Zealand? I let my little Lord of the Rings heart nerd out with even more ideas: Let’s do one of the multi-day Great Hikes! Let’s visit every filming location! Let’s learn about Maori culture! That’s when I looked at my three-week plan and thought, “Oh crap. I need help making all of this work.”

It’s funny: As a type B, slow travel kind of girlie, I usually prefer to figure things out as I go with only a few reservations set. But I could feel myself getting pulled into the mentality my mother instilled in me: “This is the only time you’re ever going to visit this place, so you’d better see it all.” It’s hard not to get caught up in the excitement of a new place–and simultaneously overwhelmed with how much there is to see.

How much flexibility do you have around the time of year to go and how much time you have to travel? What time constraints do you have to be mindful of?

Weather is a huge factor since New Zealand is in the southern hemisphere, so the best time to visit is December through March. Even though we’re getting married in October, we decided to wait two months and take our honeymoon just after the holidays. That also gives us a few more days of vacation, but we also have to be mindful of New Years Day closures.

Flying to the other side of the world takes a few days and we want to give ourselves time at the beginning of the trip to recover from jetlag (at a resort, if possible). It’s also close to the international date line, so we need to be sure we didn’t lose an entire day…somehow. (TBH, I don’t really understand how the date line works and am mostly nervous that I’d book a hotel on the wrong day.)

We also need to consider how everything fit together: How much time will we need between big flights? Should we build in rest days, or does that cut into our travel? When is it worth it to drive versus fly? It’s important to try and stay focused on the bigger picture at this point, because there are simply too many smaller details I could get sucked into.

We don’t have to get super into specifics, but as your Biggest Trip, what is your budget like and where do you want those dollars to go the farthest?

Since Michael and I are paying for our wedding and honeymoon ourselves, we have to be clever about our budget, using a combination of savings, deals, and wedding gifts. I know we can be cheap once we were there between the cheap activities (hiking) and accommodations (camping), and as someone who defaults to driving, I’m not too concerned about spending money getting around once we get to our destination, but I am worried about the flights. Honestly, flying is rough for me. But I don’t want my aversion to keep me from exploring the world. So I am more willing to spend money on the big international flights for fewer layovers, (slightly) more comfortable seating, and general ease to get us there.

Getting Down to Brass Tacks: Lessons in Long-Term Trip Planning

Taking all this into consideration, we landed (pun unintended) on a few key lessons and takeaways for their trip, as well as any trip you may decide to go on in the future.

Lesson #1: Understand Your Limits

As someone who just spent three weeks in essentially three different regions (Shanghai, Hong Kong, and Taipei), I knew firsthand that what seemed doable on paper might be wildly different in the moment. So when I originally saw Emily’s original itinerary, I was a little hesitant that this would be sustainable even with three weeks to work within:

I completely understand the desire to maximize the time that you have, especially if you’re traveling to such a far destination. But since it was also their honeymoon, I asked them: If you had to pick just one or two destinations to spend your time in, what would make the cut?

We also gently covered the fact that two days of travel time, jet lag, cancelled flights, or bad weather might make traveling across regions impossible. For example, one bad storm, and you’d be stranded for a day or two. Or perhaps the sheer length of travel time necessitated a day of rest they may not otherwise think about.

Eventually, Emily said: “After talking it out, I could tell that the plan I had on paper would never translate into a trip we’d actually enjoy, so we’ve decided to hone in on three things: the national park; a few key LotR locations; and van life.”

After that back and forth, Emily and Michael landed on eventually nixing the majority of their time in the North Island of New Zealand, instead prioritizing their time in American Samoa, Samoa, and the South Island of New Zealand.

Lesson #2: How to Run the Numbers & Manage Logistics

Honeymoon destinations are often far-off and romantic: The Maldives, Fiji, Bora Bora, and in this case, Samoa and American Samoa. But that also means you have to work within the bounds of that particular place; for example, many islands only have one departing and one returning flight a day.

In Emily and Michael’s case, their goal to start in Samoa (Apia) meant flights were looking like $4,500/person round-trip. But we found that, with the help of Google Flights, if they were open to starting in American Samoa (Pago Pago) with a quick flight over, that price quickly came down to $2,000/person. But before moving forward, you have to know: How do you get from one to the other—and are the cost savings of those inter-island flights worthwhile?

After some research, we ultimately decided the best use of their time and money would be to fly into American Samoa, visit the local National Park there, head to Samoa for a few days of relaxation, and then head on to New Zealand. This kept prices within their budget (essentially an additional $700, but far cheaper than $4,500 a pop) while also managing the times and availability of flights and ferries between each region.

In my own experience, I’ve booked a flight from one destination thinking I’ll just fly to an island nearby and how expensive could that be? Turns out, very. So just be sure to do your own due diligence and run all the numbers and all the various routes.

Lesson #3: Know When to Splurge & When to Book

When you’re planning to visit multiple places—or frankly, when you’re on a bucket list trip—don’t just optimize for price.

While Emily and Michael could save $200/person for their leg between Samoa and New Zealand, they’d also have to deal with multi-hour layovers. That might be okay if you’ve got endless time to spare, but when it’s your honeymoon and you have multiple places to get to, it’s simply easier to pick the most efficient route. (Not to mention Emily’s note that she doesn’t love flying.) I promise you, you’d rather be at your destination earlier, than wasting time away in an airport lounge, hungry and tired.

Along this same vein, I would argue the most important parts of a trip to book first are your departing and returning flights, rather than any inter-country transportation or hotels—those are the ones most likely to sell out first.

Lesson #4: Honor Everyone’s Preferences

In some ways, planning a multi-country, multi-week honeymoon is great practice for marriage. It’s the basis for compromise, especially when you’re very different people. Or when you want to balance relaxing versus adventuring, even if you’re not typically a “relaxation” person. But when both people are contributing to the trip (financially, mentally, so on), everyone’s needs deserve to be met.

An exercise my husband and I did while planning our wedding might work here, too: Write down all the activities or destinations you want to see while traveling. Then each person privately ranks them all in order of importance. Afterwards, come back together, and see where you’ve all landed and where you can negotiate to make sure everyone’s satisfied. In the case of our wedding, we realized neither of us cared much about the cake but were very interested in making sure the food was top-tier. That helped us to manage our financial priorities and where we spent the bulk of our budget.

In Emily and Michael’s case, this ultimately meant compromising on the amount of time spent in the van versus in hotels, upgrading to comfort seats given the long travel days, realizing how important visiting this national park in Samoa was to Emily, and honoring Michael’s preference to not bounce around too much.

Finally, it’s crucial to remember: Just because you love to adventure or loaf around at home doesn’t mean that may be the case there. You could come down with food poisoning, and decide that you need to slow down for the majority of the trip. Or, you could be so inspired you want to trek across mountains you’ve never considered before. We know travel changes you, so keep that in mind when you’re planning a Bucket List-level trip.

Where We Landed

After 90 minutes of discussion, all three of us felt like we were in a solid place for them to move forward with their plans, albeit different than what they originally envisioned: They would fly from Atlanta to American Samoa first, head to Samoa for some relaxation, make their way to New Zealand for two weeks of adventuring and van life (with fewer stops than anticipated), and then return home from Auckland.

The updated budget would still be in line with what they hoped to spend, and they would still get that taste of slower, deeper travel of knowing a place—reminiscent of Emily’s earlier days on the road—without compromising on what mattered to both of them.

With the countdown running for a few more months, we won’t know how their trip went just yet. But of course, if you want to hear how it turned out, follow on her Substack.

I asked Emily how she felt, given the larger shifts in their itinerary:

First and foremost: relieved. It feels great to have another perspective weigh in on our plans, especially given the duration and expense. There will definitely be a part of me that wishes I could include everything (missing Rivendale will be a bummer) but I also know we’ll have a better time if we spend more time in fewer places. We’ll get more time to learn about each place and, God willing, actually relax. I’m also glad we finalized the big pillars yet still have time to figure out the day-to-day details. There’s plenty of room to be flexible and live in the moment, which is the way we want to travel. Ultimately, this trip is to commemorate starting our lives together–nothing is stopping us from going back, no matter how different the circumstances.

In some ways, two weeks on the South Island with a van and without a fixed agenda is essentially aligned with the same life Emily’s lived for years, just transplanted to the other side of the world and a lifelong partner to experience it with. And ultimately, the "see it all" pressure was never really hers; it was inherited. So the planning process was actually about setting it back down—about minimizing the friction and maximizing the enjoyment. And that’s what all life-changing trips should do.

• 🎉 Thanks to everyone who commented on last week’s giveaway—it was so fun to hear where everyone’s itching to go one day in their lives (and now maybe this post will help you do it soon). The winner of a $100 gift card to the vendor of their choice is… ! Please DM me to claim.

• 🤗 Even when we can’t travel the way we dream of, we can still find joy through anticipation. Loved this roundup from with 15 easy ways to find small delights in the every day.

• 👀 AmEx has an enticing new transfer bonus this month: Through June 20, you can get a 25% bonus transferring AmEx points to Air France/KLM Flying Blue. Flying Blue is probably my #1 redemption partner to Europe (think 30–40k points RT), so I’m plotting on ways to use this. (Frequent Miler)

• 🌱 The embodiment of slow travel: This essay from Jenny Odell, the well-known author of How to Do Nothing. “Listen deeply enough, and the act becomes more than a collection of impressions. It can instead demonstrate a world with far more participants, and participation, than you had ever before imagined. It is the door to a dialogue between earthly entities. And it opens onto a world that I personally find far less lonely.”

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Tomorrow, I head to Europe for my first international solo trip in a looong time—I can’t wait to have some well-deserved down time in the place I love most followed by a Harry Styles concert and a jaunt around Paris. More to come. x —Henah

Welcome back to Departure, the weekly newsletter focused on slow travel, quiet travel, and travel for women. I’m beaming today because we officially reach 4,000 subscribers, and that is no small feat.

To celebrate, I’m awarding one reader a $100 gift card to the vendor of their choice. To enter: Like this post and comment with a bucket list destination you hope to see in your lifetime. Winner to be announced next edition. And as always, thank you for your ongoing support. 💕

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I originally hoped to do a feature this week on sleep and jet lag as I’ve tested out products for months, but the sources I heard from weren’t at the quality I wanted. So, I’ll be pushing that piece back until I can speak to more qualified experts. In the meantime…

How to Make the Best of Bad Weather

Last weekend, we made the seven hour drive to New Orleans, only to be hit with nonstop thunderstorms and flash flooding. The next three days were more of the same: Heavy rains, cancelled plans, and taking care of a pup deeply afraid of fireworks. The journey back home was similar to the drive there, wipers on full speed, hazard lights blinking, unable to see more than ten or twenty feet ahead of us.

It turns out, the weather was from a powerful El Niño forming, stretching hundreds of miles across the Eastern side of the United States. (This feels wildly underreported for how many people it’s affecting.) Causes aside—read: climate change—rainy weather can affect our travel plans, but it doesn’t have to make or break them.

Between this trip, the time we were hit by a Mediterranean hurricane in Santorini and stranded for several days, and a very wet few days in Miami on a friend’s milestone birthday trip, I am no stranger to shifting plans and finding new things to do. Keep these activities handy for the next time the weather isn’t going your way:

1. Live Like a Local

By this, I mean: Head to the nearest grocery store and peruse the aisles; grab new-to-you foods to try. Find a laundromat to throw in a load and chat with locals as you wait. Stop by a covered food hall and snack your way through the booths. Head to a nearby brewery and watch a sports game with the regulars.

(This could also be a good time to test drive the Google “Ask Maps” feature! Prompt it to create a rainy day itinerary across your destination.)

Ultimately, immerse yourself in their rhythms and ways of life: This is often one of the best practices of “slow travel” we try to do anyway.

2. Treat Your Time Like a Staycation

Because our most recent trip was our eighth (!) time in New Orleans, we didn’t feel too bad about staying in bed or taking luxuriously long afternoon naps as it stormed outside. If the hotel had had a spa, I probably would’ve booked a massage.

Maybe if you’re staying somewhere with a fireplace or a library, you can situate yourself in a cozy corner for the afternoon. Order room service, baby! Catch up on your sleep, your reading, your Netflix queue, your Nintendo Switch games.

Not all travel has to be exploratory; sometimes, it can simply offer a chance to breathe and step away from your day-to-day life.

3. Stop by Museums & Cultural Landmarks

This one seems the most obvious, I know, but my husband and I have really fallen in love with museums lately. We’ve visited six in the last few months, and every single one has been a worthwhile use of time—especially those that nod to a destination’s local culture or community.

Don’t sleep on niche museums either—we’ve stepped foot into one-room collections that we still talk about years later, like the Jazz Museum in Harlem or the Voodoo Museum in NOLA. You can find museums or landmarks near your location via the local tourism website, Atlas Obscura or the Niche Museums directory. (Just check their business hours before you head over.)

If you’re not a museum person, maybe you can find a local cinema that has subtitles, watch a live music set by a local band, or pop in and out of boutiques in a shopping district just to understand the arts and goods made in the area.

4. Book a Class or Learn a New Skill

In the pandemic, we became big fans of Airbnb’s online experiences. If you don’t feel like leaving your hotel room (fair), you can still learn something new via an online tour or on YouTube. If you’re with friends or family, try a PowerPoint party or skill-sharing together.

If you can brave the weather, consider a last-minute class that often have cancellations or allow drop-in attendance: Cooking classes, pottery workshops, spray paint tutorials. CourseHorse and Eventbrite are great for finding these, as well as the Events Calendar for most city websites. (Another tip: Find cool spaces or classes you want to check out on social media the weeks before you go, and they’ll often share last-minute openings or opportunities there.)

5. Give Into the Rain

Listen, I’m not above a moody moment, where you can lean into your feelings:

Frankly, some destinations are more beautiful in hazy or rainy weather: Amsterdam, Thailand, Seattle. So if you’re willing to get a little wet, take a walk in the rain anyway and enjoy the moment.

Walk slowly and with intention: What might you notice about a city’s infrastructure? What food or drink is this city known for when craving warmth and coziness? Are you experiencing a unique micro-climate? How might rain affect tourism more broadly?

If ambling outside with an umbrella isn’t of interest, perhaps you can divert to a local onsen or bathhouse where the sound of rain lets you unwind and relax. See also: #2, staycation.

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I still get frustrated by plans thwarted by bad weather—I had a vision in mind, darn it! But I also appreciate that it gives us permission to slow down and simmer in the moment. And I hope that reframe is worth considering on your next trip, too.

PS: This is a good time to mention how invaluable travel insurance can be, especially if you have coverage for hurricane and weather conditions, or Cancel for Any Reason/Interruption for Any Reason policies. May you never have to use it, but better to be prepared.

• 🎧 During the drier hours of the road trip home, my husband and I listened to Who Blew Up the Guidestones? from the Atlanta Journal-Constitution. If you’re looking for an intriguing mystery to uncover over the span of a few hours, this is it. It reminded me of S-Town, and you’ll hear about everything from the KKK to eugenics to QAnon in here. (And yes, the end is satisfying.)

• 🚗 Speaking of road trips: When I was eight years old, my family embarked on a three-week trip across the States. My parents removed the middle seat to give my brother and me some space to splay out and play on the long drives, and it became a core memory. This Texas Highway piece about a family traversing 3,000 miles all over Texas was deeply nostalgic and brought a smile to my face. Insert a corny ChatGPT line about how maybe the age-old question isn’t, “Are we there yet?” but that about the journey instead.

• ✈️ Still hoping to book a flight this year? shared the top cities where affordable flights have been most consistent over the last year. Some of my favorite trips were based on last-minute deals, so it’s never bad idea to scope out.

• 🪒 In an effort to stop buying laser hair removal sessions, I purchased this at-home device and have been pretty happy with the results! A year later, and my legs can go up to a week now without shaving. It’s not cheap, but it’s definitely cheaper than laser packages… and much less painful, private, and easy to use as we kick off summer.

• 🥲 An oldie but a goodie: “Travel isn’t always pretty.”

In the next week, I’ll be traveling to Florida, New York, and back to Europe—wish me luck, and I’ll see you then! x —Henah

Welcome back to Departure, your weekly travel newsletter. I’m back this week sharing about the second stop on our recent trip to Asia: Hong Kong. (You can find our first stop in Shanghai here.) The guide is quite long so you may need to open this in your browser, but I hope it feels like a thorough and handy resource. But first…

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*CW: This post mentions loss of a loved one and grief.

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This edition is sponsored by Sky Key, a product I personally use for every flight.

Sky Key monitors your flights from the time you book. If the price drops, Sky Key automatically rebooks the same flight (yes, in the same seats!) while refunding you the difference. Sky Key only makes money (25% of savings) when they save you some—no savings, no fee. In th…

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This week’s edition is long but one of the best conversations I’ve ever had, so I encourage you to open it in full in your email. 💌

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This article was sponsored by Adobe. As always, all opinions and ideas are entirely my own.

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As part of my community-based ethos, I shared earlier this year that we’d launch guest guides. These enable me to spotlight other women travelers from around the globe…

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It turns out, we don’t really remember a destination objectively—we remember a place by how we arrived there.

I realized this in Shanghai last week, and it changed how I think about arrival days. It taught me that the first 24 hours might actually matter more than the rest of a trip.

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It has been another heavy week in the world, and I hope you’re all hanging in there.

Earlier this week, I opened my Instagram DMs and the subscriber chat for AMA on all things travel. We used to do these when we first launched Departure, and I thought it’d be a nice source of levity (and a helpful resource) to do one today.

This email gets a little long s…

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