Build Connection, Not Conflict
Hot take: The key to amazing group travel isn’t matching flights, or matching t-shirts; it’s about matching expectations.
Whether you're traveling with your partner, your siblings, your best friends, or a multi-gen crew, the right trip has the power to bring people closer in ways everyday life rarely allows. And like any strong relationship, it starts with good communication, clear expectations, and shared excitement.
Let’s talk about how to plan it.
I love me some shared travel. I love the inside jokes, I love the support, I love seeing people I thought I knew well absolutely excel in brand new ways. Really, it’s just the best thing to bring me back to joy. And science backs that up (yay science!).
In their book, Look Again: The Power of Noticing What Was Always There, (and yes, it’s as good as it sounds) authors Tali Sharot and Cass R. Sunstein dive into how habituation can make us numb to awesome and not-so-awesome things. But change something up? It’s fresh eyes, baby. Travel does that. It gets us out of our routines and into new experiences. Here’s why shared travel does more than just double the fun, it multiplies the benefits in powerful ways:
You become a ‘travel team’. There are tangible goals during travel, big and little. From navigating a packed bazaar to diplomatically declining unnecessary car rental insurance; there are so many wins to be had. Every single one can be a team victory and that builds bonds.
It’s still a small-ish team. You get to practice different roles and being in a new setting does make that easier. Leader, cheerleader, observer, planner, taste-tester, reality-checker, and more are all roles that are needed at different times. New places and experiences invite you to try them out and practice relating to each other in new ways.
The happiness lingers. As Sharot and Sunstein remind us, experiences don’t fade like stuff does: “While satisfaction with material goods falls sharply over time, satisfaction with experiences does not decline. Research shows that it often increases!”
Common Pitfalls in Group Travel
If you read that last section and thought, “Uh, what now? That is not how it’s ever gone for me”—you’re not alone. There are a myriad of common pitfalls and challenges that come with group travel. Anyone who has scheduled dinner for a group larger than four knows this to be true. Here are three common challenges and how to tackle them:
1) “Oh, I don’t know. You decide.”
And then they immediately reject all suggestions, and finally ‘settle’ on one of the ideas only to complain the whole time. Truth time? I’ve been her. I don’t really know what I want to do, and am hoping for someone else to magically know. (Spoiler: they never do.)
If this is you? Choose to experience whatever is chosen with curiosity. In this kind of funk, it can be hard to muster a strong ‘yes!’, but maybe a ‘well, that’s interesting’ is a good place to start. If this is someone you’re traveling with? Try offering options. Sometimes the world of choices is too much, but if you offer three options that you’re happy with, you’ll end up somewhere you’re both excited about.
2) The great chill vs. thrill debate.
Beaches and umbrella drinks may define vacation for you, but for your partner? They may thrive on action and adventure. Does this mean you can’t travel together? No, but it does mean that compromise wins. That balance can look different for everyone, on every trip. And remember, solo adventures can occur during shared travel. Sometimes the most fun is getting caught up on each other’s day.
3) Mood swings and miscommunication.
Travel turns up the volume on everything, including misunderstandings. Add in jet lag, low blood sugar, or missing luggage, and suddenly your mild-mannered bestie is breathing fire over a bus schedule. It happens! Normalize the occasional grumpy moment, check in often, and remember: snacks, shade, and sleep solve more than you think.
The theme through all of this? Communicate. Speak up. Ask questions. Clarify. Give yourself and your travel companions grace. When something does happen, shake it off, drink some water, and reset. You’ve got a travel team worth cheering for.
There’s no spreadsheet that guarantees perfect travel harmony, but there is a mindset that makes all the difference. If you want shared travel that deepens connection and builds trust, start with these three tools:
Curiosity:
Have everyone plan a day. Transportation, activities, food, the whole shebang. You’ll quickly see what lights them up. And when someone gets to “host” their dream day, even on a shared trip, it builds both confidence and connection.
Not your day? Remain curious. Let yourself experience the trip through their eyes. You’ll learn so much more than just what they like to eat.
Trust:
Things will go wrong. Flights get delayed. Reservations disappear. People get cranky. The magic isn’t in avoiding these things, it’s in how you handle them together.
On one of my brother’s favorite trips, he lost his wallet on the very last day. It could have wrecked the whole vibe. But he had his passport, some backup cash, and a sense of humor. That’s all it took to pivot.
Trust each other. Trust that you’ll figure it out. And have some backup cash.
Joy:
This one’s easy to forget in the logistics shuffle. But joy isn’t always loud. It’s sometimes a quiet coffee with someone you love. Or laughing about a wildly wrong turn. Or dancing at a street festival you didn’t plan on.
When the stress starts creeping in, ask: How can we make this moment more joyful? It’s an incredible reframe.
Sure, matching t-shirts are cute. But matching expectations? That’s the real travel win.
So build your dream shared travel trip with intention. Ask the big questions. Share your wishlist. Laugh when it all goes sideways. And celebrate the tiny moments of magic that only happen when you travel together.
Want help planning a trip that deepens connection and leaves room for joy? I’d love to be part of your travel team.