Traveling With Others
A solo traveler's guide to not losing your mind.
A solo traveler's guide to not losing your mind.
I typically travel alone. Have for years. Most of my trips, I take solo. So when people ask me about group travel, I laugh — I'm the last person you'd think to ask.
But that's exactly why I can help.
I've watched group trips implode in real time — over a table of cold tapas, in line for a museum, at 3 AM on a rooftop in Mexico City. I've seen friendships tested at 6 AM in a train station. I've learned what makes groups work by spending a decade deliberately avoiding them, and by watching from the next table over when they don't.
Here's what I know. The rules are simple. Most people break them anyway.
The nine rules.
Pick your people carefully.
Rule 01This is everything. Not your best friends from college — your travel people. The ones who move at your speed, who see a closed museum and find three other things instead, who don't need a spreadsheet to have fun.
Test them first. A weekend trip reveals everything. If someone checks their phone every five minutes at dinner, they're not your person for a two-week adventure. If someone can't adjust when the plan falls apart, they're definitely not.
Your travel people might not be the people you text every day. That's okay. The overlap is smaller than you think — and bigger than you're willing to admit.
Plan every single minute.
Rule 02The best trips I've watched as an outsider are the ones where people book the anchor moments — flights, one must-see restaurant, maybe a day trip — and leave the rest open.
Someone discovers a café. You take a wrong turn and find a neighborhood nobody planned for. A local tells you about a thing happening tonight that isn't on any list. That's where the actual story lives. A minute-by-minute itinerary kills the magic before you even pack.
Plan the skeleton. Let the meat happen.
Plan the skeleton. Let the meat happen.— Rule 02
Have the money conversation upfront.
Rule 03This one kills groups. Quietly. Expensively.
Talk about budget before you book. Not awkwardly — directly. "This trip is $X per person for accommodation, food, activities. Does that work?" If someone's expecting $500 and you're at $1,500, that resentment builds silently and explodes in Lisbon on day eight, at a restaurant nobody wanted to go to.
Say the number. Agree or don't. Then track it as you go — who paid for what, who owes whom. The trip shouldn't end with someone doing math on a Google Sheet at the airport.
For the planning side, how to plan a two-week trip from scratch has a section on the conversation to have before you book, and booking accommodation that isn't a tourist trap helps when a group has to agree on a neighbourhood. If you would rather go alone after all, deciding where to travel solo is a good place to start.
Assume everyone wants the same experience.
Rule 04One person wants museums. One person wants to sleep until noon. One person has dietary restrictions the group hasn't thought about. One person wants to party until 4 AM. One person wants to read a novel by a pool.
Stop trying to make everyone happy simultaneously. It's the fastest way to make nobody happy.
Build in solo time. Explicitly. "Tomorrow morning, everyone does their own thing until 2 PM." People love this more than you'd think. They come back recharged, with stories, ready to be together. The group time gets better when you've had a break from it.
Have a person who navigates.
Rule 05Not a control freak. A navigator. Someone who checked the metro map, knows where you're going, makes the call when you're lost. Rotates if you want, but in any given moment, one person is steering.
Groups without a navigator become a committee of five people standing at a corner staring at Google Maps, arguing about which way is north. I have watched this exact scene in more cities than I can count. It's always the same.
Pick a navigator for each leg. Let them do their job. Save your opinions for where to eat.
Let one person's mood run the show.
Rule 06Someone's tired. Someone's frustrated. Someone's homesick. Normal. Not an emergency.
The trip doesn't pause. You acknowledge it, you give them space if they need it, and then you move forward. The groups I've seen fall apart are the ones where everyone starts tiptoeing around one person's energy. That's not travel — that's babysitting.
Everyone gets one bad afternoon. Nobody gets a bad week.
That's not travel. That's babysitting.— Rule 06
Eat separately sometimes.
Rule 07This sounds weird. It's not.
Split up for dinner. One group hits the tapas bar, one group goes vegetarian, one person gets room service and reads a book. You reconvene the next morning with stories instead of resentment. You actually want to see each other at breakfast instead of being sick of each other by day four.
You're not obligated to every meal together. You didn't come on this trip to eat the exact same dinner as five other adults. Let the trip breathe.
Bring unresolved conflict.
Rule 08If you're traveling with someone you're mad at, don't.
Seriously. That tension doesn't get better in a foreign country. It compounds. It leaks into dinners. It turns a missed train into a referendum on the friendship. I've watched a trip to Croatia end a seven-year friendship — not because of the trip, but because of what they brought with them onto the plane.
Solve it before you book the flight, or travel with someone else. No exceptions.
Have a “we're doing this” moment.
Rule 09One non-negotiable thing everyone commits to.
Could be a hike. A meal. A sunset spot. A weird local tradition. A bar your friend swears has the best something-or-other. Something you all show up for, no matter what. Rain, hangover, bad directions — doesn't matter.
It's the glue. Years later, that's the moment people remember. Not the hotel, not the flight, not the €14 coffee. The thing you all decided to do together and then actually did.
This isn't about tools. It's about honesty.
Group travel works when everyone's honest about what they want and flexible about how to get it. It fails when people pretend to be chill and then silently resent every decision made without their input.
The groups that last are the ones where someone says "I need quiet time" and nobody takes it personally. Where someone suggests a detour and nobody fights it. Where money is clear, expectations are low, and the goal is to have an adventure together — not to perform togetherness for Instagram.
I still travel solo most of the time. But I've learned enough to know: the right group, the right mindset, the right amount of structure mixed with chaos — that's when group travel actually sings. And when it sings, nothing else comes close.
The key is picking people who get that. And being honest about whether you're one of them.