You think you know your friends. You have known them for years. You have gone to weddings together and helped them move apartments. You think you are solid.
Then you go to Italy with them for ten days.
By Day 3, you realize you don't actually know them at all. You didn't know that Dave takes forty-five minutes to shower. You didn't know that Sarah gets "hangry" if she doesn't eat by 11:30 AM sharp. You didn't know that Mike is the type of person who forgets his wallet at the hotel. Twice.
Traveling solo is easy because you only have to manage your own neuroses. Traveling in a group is just politics with better scenery.
I have planned bachelor parties, family reunions, and random weekend getaways. I have seen best friends stop speaking to each other over a dinner check.
If you want to come home with the same number of friends you left with, you need to follow these three laws.
Law 1: The "Zero Minute" Repayment Policy
Money is the number one reason group trips fall apart. It breeds resentment faster than anything else.
Here is the scenario. You are at a beach bar. The bill comes. It is chaotic. The waiter looks stressed. One person steps up and says "I got it, just Venmo me."
That person is a hero. They just saved the group from twenty minutes of doing math on a napkin.
Here is the rule. You pay them back immediately.
Not when you get back to the hotel. Not tomorrow morning. You pull out your phone at the table and you send the money.
If the notification doesn't hit their phone before they sign the receipt, you are wrong.
When you make someone chase you for twenty bucks, you aren't just being annoying. You are making them feel petty for asking for their own money back. Don't be that person.
Law 2: The Planner is Not the Parent
Every group has one person who naturally takes charge. They book the Airbnb. They find the flight deals. They make the reservation for dinner.
The problem is that the rest of the group often treats this person like a camp counselor.
"What time is the car coming?" "Where is the restaurant?" "Do I need a jacket?"
Stop asking the planner these questions. The planner is on vacation too. They are not your personal assistant.
If you are not the planner, your job is to be a good "First Mate."
That means you look at the calendar yourself. You check the weather yourself. You figure out how to get the keys from the lockbox so the planner doesn't have to do it.
If someone did the work to get you there, the least you can do is figure out where "there" is.
Law 3: Mandatory Apart Time
There is a weird pressure on group trips to do everything together. We eat breakfast together. We walk to the museum together. We sit on the beach together.
This is a mistake.
Human beings are not designed to spend 24 hours a day with six other people. It doesn't matter how much you love them. Eventually, someone breathing too loudly will make you want to scream.
You need to build "Apart Time" into the schedule.
I usually make the hours between 4 PM and 7 PM a "No Group Zone."
If you want to nap, go nap. If you want to go for a run, go run. If you want to sit in a cafe and scroll through Instagram without talking to anyone, do that.
When you meet back up for dinner at 8 PM, everyone is refreshed. You actually have new things to talk about because you didn't spend every single second of the day staring at the same things.
A little bit of distance keeps the group sane.
The Bottom Line
Group travel is high risk and high reward. When it works, it is the best thing in the world. When it fails, it is a nightmare.
Respect the money. Respect the planner. And for the love of god, take a break from each other every once in a while.