4 Lessons for Planning the Biggest Trip of Your Life
Balancing Type A and Type B travel, a worthwhile transfer bonus, and announcing our giveaway winner.
This edition is available to all subscribers, courtesy of our sponsor Sky Key.
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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 Emily Edwards 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… Kate S! 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 Amelia Wilson 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.”
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
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The “see it all” pressure is real, especially when you’re going that far and spending that much.
I like that they cut it back to the trip they’d actually enjoy. Fewer stops, less rushing, time to be tired, and room for it to feel like a honeymoon.
Congratulations, Emily and Michael! I loved the collaborative effort in this post and in the honeymoon planning.