Greetings from New York City, where I’m posted up for work this week. It’s officially fall, with crisp morning temperatures and a cool evening breeze, and I am savoring every minute.
It felt like the perfect weather to settle in on the couch and answer some of your questions—from how I can afford to travel regularly to who I’m following nowadays for travel expertise, I hope you enjoy this Ask Me Anything. If you have other questions, leave them in the comments for consideration in my next AMA!
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“Where would you go for a week last-minute in October?” —Alison M.
October is my favorite month—it’s gorgeous nearly everywhere, and not too cold just yet. I would head to upstate New York, New England, or the Catskills to see the foliage change and curl up with a book by a cozy fire every evening.
It’s also the beginning of off-season/shoulder season in Europe, so I would look there if there’s a place you’ve been wanting to visit; Transylvania in Romania could fit the mood around Halloween, while Madeira, Portugal, Cyprus or Malta, or the Azores might be less-crowded destinations that still feel a little like “Mediterranean summer.”
“Who are your top 5 travel pages that you’ve discovered recently that would be new to us? Substack or IG!” —Jeannie K.
Truthfully, I could do a better job of scoping out new sources or follows—I’m a creature of habit, and my daily media diet is pretty routine. That said, I am a huge fan of Juliet Kinsman (sustainability and travel editor), Katalina Mayorga (founder of El Camino Travel and behind The Business of Experiences), Stephen Satterfield (food journalist and textile operator), Daniel Scheffler of Without Maps, and Monica Mendal of So There’s This Place.
How do I talk to my partner about traveling solo and help him worry less about my safety?” —Samantha P.
If you can navigate any mid- to major-sized city in the US alone, I feel confident you can travel solo anywhere! That said, I have several safety tips:
Always share your location with someone you trust, ideally someone in the vicinity in case of emergency.
Book a stay in either a short-term rental like an Airbnb with a personal host who can meet you, or a larger chain like a hotel with a concierge.
Prioritize a good location over anything else; it’s worth paying extra for the peace of mind.
Schedule your flight to land or your train to arrive during daylight hours.
Look for reviews that mention safety specifically, particularly ones that include “solo traveler” in the review. What’s safe for a couple or family might feel different for you.
Give your partner a thorough rundown of your plan before you head out, pre-establish times to connect, follow the above, and trust your gut. You got this.
“Super curious about your career journey to travel writing—what has that looked like? Do you have a day job?” —Alexandra M.
I do! I’ve worked at Morning Brew for nearly five years, four of which were on the brand Money with Katie. I’m now a managing producer for multimedia, so I work with reporters and editors on stories across B2B news. I’m incredibly grateful for the stability and flexibility my full-time work allows me (being remote with unlimited PTO is a true gift), because it gives me a lot of space to dedicate to Departure.
The TL;DR of my journey to travel writing: My co-founder and I worked in digital media and often pitched travel stories, but they were never really a dedicated vertical. We decided to try building out a travel-dedicated Substack in the summer of 2024, and when she rolled off due to time constraints, I told myself I’d keep writing weekly until it stopped being fun.
Two years later, here I am—across 80+ countries, 4,000+ readers, and landing partnerships I’ve only ever dreamed of. I feel very, very lucky, in addition to working very, very hard (new content every single week alongside a full-time job and other commitments isn’t always easy). This is to say: It’s still fun! Please go pursue the thing you can’t stop thinking about.
“How does someone afford to travel so often? Not judging, I want to do it too! ;)” —Kristin G.
The honest truth is that my husband and I are both high earners in our day jobs, and we don’t (yet) have children. Ultimately, that combination leaves a lot of room in our budget—when we prioritize it. My husband does not care for travel the way I do, so sometimes we don’t prioritize it and redirect those funds to house projects or local entertainment.
I also almost never spend money on clothes, shoes, bags, etc. I’m not a big shopper (given my background in ethical and sustainable fashion), and I do not have Amazon Prime, so most of my disposable income goes toward home decor, books, or travel.
Departure has also grown substantially; this will be my first year making five figures of revenue from my newsletter (never thought I’d be able to type that sentence!), so I re-invest that money into fueling more trips.
“How to approach travel on a super budget? Tips on just starting?” —Katie L.
Back in the 2010s, I was making anywhere between $40,000 and $60,000 working in New York City, which is to say, my income did not go very far. Getting into points and miles was actually by necessity, and it allowed me to see the world without worrying about racking up debt.
I recommend easing into the points and miles game. A reliable under-$100 card with a valuable sign-up bonus like the Chase Sapphire Preferred is almost always my recommendation, as that can yield quite a few flights. In addition, you could look at hostels and house-swapping to bring down your accommodation costs. There were some helpful resources and comments in last week’s edition about booking a last-minute trip that might be of use, too.
Two other tips:
My husband and I prioritized travel in those earlier, lower-income days by agreeing to one international trip and one to two domestic trips a year—by making it a sustainable line item in our budget, we were able to plan and make it happen without feeling overly stretched. It requires intention and time, but so does anything when you’re starting for the first time!
Remember that you don’t have to go to the airport: Day trips, weekend trips, and road trips count as travel. Getting out of your comfort zone and experiencing a new-to-you part of the world is the point, and that can be close to home.
“How do you slow down if you’re a FOMO traveler? I’m able to slow down if it’s a city I’ve been to, but when I’m in a city for the first time, I want to see it all! And it drives my family crazy.” —Kristin G.
I understand the inclination, especially if it’s been a place on your bucket list for years and years. For me, though, I’ve learned that I savor my trips more if I take my time and really nail down what I would enjoy seeing versus what I feel like I have to see. For example, yes, I could’ve gone to the Eiffel Tower twice this year when I was in Paris, but I instead traded that time for vintage markets because I knew it would fill my cup more. Otherwise, it can often feel like I’m checking off boxes but not really immersing myself in the experience.
The second reminder is that these places will almost always exist if you want to return, so it’s worth sitting down with your family and ranking what’s most important on a first trip—and what can wait. FOMO doesn’t have to mean missing out forever.
Lastly, I slow down because I have to—chronic illness makes it difficult to do more than one to two major things a day. But in some ways, I find it a blessing that it forces me to take each minute as it comes and to not pack my days. The memories I smile at most when I return weren’t really about rushing to see all the sights, but about the small moments focused on what I really loved.
"How do you plan your itineraries?” —Navya L.
I don’t really have a set formula, beyond building in buffer time after arrival and before departing. It depends on a multitude of factors like availability, distance from our accommodations, and opening hours, but if I were to plan a new trip from scratch right now…
I’d look at the dates I want to go or the destination(s) I’m interested in, and book when ready.
Then I’d compile a small list of activities I want to do and where they would take place, before booking lodging. I want to make sure where I end up is close to all the experiences, if possible.
I’d reserve my accommodations, checking for credit card cash-back offers or credits.
I’d start planning out each day based on knowledge of my momentum and energy flows (see above about only coordinating one to two activities a day). I always leave a considerable amount of wiggle room for impromptu wandering, last-minute reservations, or delays/illness.
That’s pretty much it! I try not to overcomplicate it, and aim to be intentional.
“Thinking about joining a group travel trip for my first solo trip. Any brands you’d recommend?” —Jacob A.
Group trips are the perfect way to ease into solo travel thanks to the security of an established guide and itinerary. I wrote about my experience and what I’d do differently in this older post, and that would inform what I’d recommend to you now. Questions to ask yourself:
What level of adventure or activity are you looking for? There are plenty of companies that lean toward the adventurous, whereas smaller, niche tour companies might center the trip around slower, less-demanding travel.
What matters most to you? Cultural immersion like cooking classes, quick hits like walking tours of major landmarks, checking off as many countries as possible? Look for what makes you feel most engaged.
Do you need a room by yourself, and would you be willing to pay a premium for it? Most group tours require you to share a room to keep costs low, but you can pay an additional fee for your own space. At first, I was too cheap to do this, but now, I would happily splurge on a space to call my own so I can decompress after a long day.
From there, you can nail down logistics like budget, availability, and geographic locations. Some trusted operators include Flash Pack, Intrepid, Contiki, G Adventures, National Geographic Expeditions, etc., but there are also hundreds of smaller operators who are worth looking into. Good luck!
“I’m going to NYC and will have just evenings free. What are two experiences I should prioritize?” —Katie E.
Without knowing your specific interests or trip dates, I can only advise you on what I think makes New York City magical. (I grew up in New Jersey and spent most of my 20s working across Manhattan, Brooklyn, and the Bronx.)
To me, the arts and theater are essential to the spirit of the city, and while I would always recommend a Broadway show, I would also encourage you to check out smaller acts or theaters. For example, I just saw Pre-Existing Condition at the Greenwich House Theater starring Phillipa Soo, who’s best known for her work in Hamilton. Off-Broadway or even off-off-Broadway can be as incredible as the bigger shows, more intimate, and just as deserving of support.
Second, I suggest spending your evenings watching either live jazz at a club like Smalls or the Village Vanguard, or stopping by a speakeasy like Please Don’t Tell (St. Mark’s Place), Little Branch (West Village), or Raines Law Room (Chelsea or Midtown). Book reservations in advance, and scope out the hidden entrances ahead of time, but remember that finding it is sometimes half the fun. ;)
But sometimes it’s best to simply jump on the subway and head somewhere you wouldn’t normally go—like Crown Heights—and just walk around and get lost in the boutiques, bars, and restaurants. (For example, Kissa Kissa is a Japanese-style jazz kissa and vinyl listening bar in CH, with over 5,000 vinyls and different listening night themes. When else would you stumble upon a place like that?!)
“What are your recs for long-haul flights? Any must-haves?” —Tallie S.
Call me a millennial, but comfortable leggings with pockets are my go-to. I can contort my body however I need, without worrying about my passport or keys falling out. I only wear Beyond Yoga at this point. They are buttery soft, have a ton of stretch, and worth repeating: pockets.
Compression socks are a must-have; I prefer Wellow or Bombas.
I personally like to wear my Rothy’s clogs because they are extremely comfortable and adjust if your feet swell, but otherwise, a reliable pair of sneakers.
An organic cotton tee (breathable yet soft), and a sweater or blanket as an additional layer.
My Sony XM6 headphones, specifically for the noise-canceling feature. I went to Best Buy and tried on different headphones until I found ones I liked over my ears.
Dramamine (IYKYK). Can’t fly without it.
A good neck pillow (this one is my favorite). This + Dramamine + feeling warmly cocooned in my layers = decent sleep.
An extra hair tie, my ILIA lip balm (I literally do not leave the house without it), mints/gum, a hair brush, Tylenol, power banks and chargers, etc. all go in my backpack.
If you need an eye mask, this weighted sleep mask is A+.
I shared my full rundown of how I pack a carry-on bag and backpack for 10 days in this older post, but for long-haul flights, these are my non-negotiables.
“Should I move to Canada, or Boston, or East Coast—because I miss my friends and girlfriend?” —Sahira J.
This isn’t a travel question, per se, but one about the world, so I’m inclined to respond: Go where you are loved, enjoy the weather, and where you feel most alive.
😍 I had the honor of trying DedCool’s latest scent, Mocha Magic, and as always, they’ve knocked it out of the park. It’s a comforting, warm, and sensual scent with notes of espresso, toffee, and tonka bean—an ideal fall-to-winter fragrance you can bring wherever you’re headed this season.
👏 The algorithm always feeds us what it thinks we want. But what if we designed a curriculum for ourselves? I encourage the same for travel—approaching with your curiosity. (h/t Israa Nasir of The Well Guide)
🏠 Seven famous homes you can actually rent. Hit me up when I can stay at the Traitors castle, though! (CN Traveler)
🥹 Now why did this make me cry?? (h/t Lauren Quintal)
🔎 And finally:
See you next week! —Henah x
Thanks for the tips! I'll report back on how it goes 🫡