How We Plan Long Trips Without Losing Our Minds

Tips, tools, and real examples from two travelers working remotely and living abroad for months at a time.

We’ve been asked more times than we can count:
“How do you even plan a trip like that?”

The truth is—we don’t.
At least, not all at once.

What keeps us sane—especially during multi-leg journeys or working from the road—is that we plan the key pieces, and we trust the rest will unfold.

Here’s how we approach travel without burning out before we even leave home.

Our recent trip from North Carolina to Bangkok could’ve been a nightmare: three flights, two hotel stays, a rental car, and a 10-hour layover in Paris. It went like this:

• A one-hour flight up to NYC
• An overnight at an airport hotel
• A 7-hour flight to Paris
• A 10-hour daytime layover (with a hotel room and real lunch)
• Then an 11-hour flight to Thailand

Sounds like a lot, right?

But we didn’t experience it all at once. We focused on one step at a time. First check-in, then security. Then a snack, then boarding. When we landed in Paris, we weren’t stressing about Bangkok—we were thinking about our hotel room, a shower, and maybe something sweet from the airport Monoprix.

We’ve learned that when we treat each leg like its own mini-adventure, we don’t get overwhelmed. We just keep moving forward—step by step.

This step-by-step mindset shows up in how we pack too. We think through each phase:

• What’s needed in the carry-on for the first flight?
• What will make the layover more comfortable?
• What should stay in the checked bag until arrival?

We also make sure we’ve got any required visas, arrival cards, and backup documents easily accessible. Even in the digital age, we print key docs. (Yes, we’re those people—and yes, it has saved us more than once.)

Some of our travel-day MVPs aren’t sexy—but they make all the difference:

These are not affiliate links. Just our real travel go-tos—no kickbacks, just honest recommendations.

• Foldable slippers for long flights and hotel room floors (shoutout to Allyson for that game-changing recommendation)
• A good eye mask and ear plugs for rest on the go
• Compression socks that save your legs on long-haul days
• A power brick that works on the plane and in your layover lounge (thank you, Isadora, for blowing my mind at that conference a few years ago—we’ve carried one ever since)
• A few wellness extras always in our bag: lip balm, hand cream, and a refreshing face spray

Bonus tip: Download your books, shows, and podcasts in advance. Don’t assume Wi-Fi will cooperate.
Case in point: Just a few hours before our 11-hour flight to Bangkok, we got an alert—no in-flight Wi-Fi available.
Thanks to our habit of downloading ahead of time, we had what we needed. But we saw plenty of fellow travelers scrambling.

And of course, the apps that help us keep it all together.

We swear by TripIt to stay organized—and it’s just one of 11 must-have travel apps we rely on regularly.

👉 Want the full list? Join our Travel Guide Library here
One email unlocks all our free guides—including our go-to travel apps, slow stay city picks, and more.

Oh, and one more thing? We’re both working as we go.

That means it’s not just sightseeing—we’re juggling meetings, writing deadlines, and real life across time zones. Planning the right things (but not everything) makes that balance possible. If we tried to script out every detail, there wouldn’t be space for our actual work—or for the joy that makes it all worth doing.

On this current trip, we know which countries we’ll be in and for how long. We’ve booked:

• Our flights between countries
• Our lodging in each location
• And a few key reservations—like visa applications and one very hard-to-get dinner spot

That’s our framework. Everything else is intentionally flexible. We’ll layer in excursions, cafes, and weekend adventures as we go—based on recommendations, local feel, and weather.

We like to say: we build the frame, and fill in the rest later.

Over time, we’ve learned that travel works best when we focus on the mission-critical:

• Where we’ll sleep
• How we’ll get there
• What needs to be booked ahead

Beyond that? We let it breathe.

We don’t need to know where we’ll eat dinner two weeks from now. That’s the fun of showing up.

Even with thoughtful planning—things go sideways.
That’s not a failure. That’s just travel.

On this latest trip, we didn’t do enough research on the airport shuttle situation in Paris. After wandering Charles de Gaulle with tired eyes, trying to figure it out, we finally gave up and grabbed a taxi. Could we have avoided it with more prep? Probably. But we also know: we can’t optimize everything.

There’s always something that doesn’t go to plan. A late train. A closed restaurant. A document we forgot to screenshot.

In the moment, it’s frustrating. But those are the stories that stick.
We’ve learned to leave space for those moments too—not just in our schedule, but in our mindset.

Jet lag is real. And instead of fighting it, we try to flow with it.

One of the benefits of long-term travel is that we’re not cramming everything into a few days. So we build in a day or two of ease when we land—no big plans, no pressure to “hit the ground running.”

We eat when we’re hungry. We nap if we need to. We go for a walk, grab groceries, maybe find coffee.

That rhythm helps us recover faster and arrive more fully.
Because nothing sets a trip off course faster than pushing your body beyond what it’s ready for.

One thing people often say about how we travel is that we make the most of time others might overlook.

If we learn that something’s fun, meaningful, or beautiful—even if it’s a bit out of the way—we’ll find a way to make magic with it.

On this recent trip, we had a layover in New Jersey. Instead of just staying near the airport, we took time to explore Jersey City—the place where we first met 18 years ago. It wasn’t part of the original plan, but it turned a layover into a little love letter to our story.

Another time, we were passing through Bacalar, Mexico—a place we’d wanted to visit for years but never managed to fit in. As our route took us close, we asked the driver to drop us off instead of heading all the way home. We spent a few nights by the lagoon and caught a bus back later. People we talked to couldn’t believe we thought to do it that way.

We also make space for side trips to reconnect with friends and family, even if it takes us slightly off course. When we were in Kuala Lumpur, we met up with our friend Steph and her family, who had recently relocated from Charlotte. We brought a few goodies from home—small things, but meaningful.
Something about seeing a familiar face in a faraway place made everything feel more connected.

And when we found out our friends Andrea and George happened to be in Mérida at the same time we were, we didn’t let it pass us by—we made sure to carve out time for dinner together. In the middle of a busy travel season, that simple evening ended up being one of the highlights.

To us, that’s what long-form travel makes possible.

We try to leave room for rerouting, for hunches, for joy that doesn’t require a reservation.

And those moments? They’re often the ones we remember most.

Whether it’s a long-haul trip or a long-term chapter, the truth is: travel doesn’t happen all at once. And you don’t have to plan it all at once either.

You just need a strong starting point, the right tools in your pocket, and the willingness to take it step by step.

If you’re planning a trip—especially a long one—ask yourself:

What matters most? What can wait? What might you let unfold on its own?

Wherever you’re headed next—whether it’s three weeks or three months—here’s your reminder:
You don’t have to figure it all out today.
Just the first few steps are enough.