How to Travel with a Group (and not go crazy)
Updated: April 19, 2023
Picking a Date
Can a trip be annoying before it even starts? Of course—just ask anyone who’s been on a group email simply trying to select a date! No one wants to sort through 30 emails with dates that work (intermixed with inside jokes sent reply all, of course). That’s why I love using Doodle. This free online tool allows you to create a poll with multiple dates. Simply email the poll to the group and everyone selects which dates work for them. Super easy!
Setting Realistic Expectations
The older I get, the more I realize that expecting too much often leads to disappointment. This is especially true when traveling with a group. It’s quite hard to get my family of four all ready and out the door at the same time. Now add grandparents, aunts, uncles and more kids to that mix and you’ve got a logistical nightmare.
Instead of being disappointed that things aren’t coming together in the exact way you imagined, go into the trip with a “what will be will be” attitude. The point is to spend time together, and if you’re stressed about a schedule or fulfilling some dream of the perfect vacation, it’ll bum you out.
Booking a House
Hotels are great, but for groups, you really can’t beat a house. It makes eating together easy—not always the case when trying to dine out with a group. Those who need to go to bed early (i.e. kids) can do so, while night owls can stay up late in the common areas. And hanging out tends to happen more organically if you’re all housed in the same spot. None of this texting back and forth about when everyone will meet up in the hotel lobby.
Figuring out Transportation
The process of renting a car has never been easier. If you rent cars regularly, you’re likely accustomed to walking down a row of available cars and just selecting one. However, if you’re traveling with a group, don’t expect the rental car company to have a SUV or minivan just hanging around. To ensure you nab a vehicle that accommodates your group, you definitely need to make a . Trust me, it’s way more fun than trying to squeeze five adults and all their gear into a Chevy Malibu.Talking about Budgets
Expectations play a huge part in the morale of a group vacation. This is especially true when it comes to budget. Some people might be willing to drop major moolah on meals or adventures; others might prefer to pack lunches and seek out free activities. Traveling with both types of people on the same trip is a recipe for resentment. Better to talk about the money stuff before you go. Yes, it can be uncomfortable, but it’s something we all should strive to be more open about. Ultimately, it will make your trip more enjoyable. And of course, if someone wants to do something special (or opt out), let ‘em! It’s their vacation, too, and no one said everyone has to do everything together.
Ensuring Everyone Chips In
We all have that one friend who suddenly has alligator arms when the check arrives. Fix that issue with technology. There are so many apps that make settling up a breeze. It’s so easy, that your younger brother is going to have to retire his regular “oh I forgot my checkbook” excuse. So instead of the headache of splitting the bill at every meal, every grocery store trip, etc., you can all take turns paying as you go.
Spending Time Together, and Apart
Just because you’re traveling as a group doesn’t mean you should spend every waking moment together. If someone needs to unwind with a book or a nap, let them, and don’t make a fuss about it.
Letting Everyone have a Say
When you’re traveling with friends or family, picking a restaurant, activity or even a radio station can sometimes feel like a battle. An old fashioned vote lets everyone voice their opinion. Conversely, you can take turns choosing.
Divvying Up Tasks
There always seems to be one person in every group who gets stuck doing all the dishes, cooking all the meals or planning everything. Unless you’re traveling with your butler (wouldn’t that be nice?), these responsibilities should be divided amongst the group. Chipping in gives everyone a little skin in the game and lessens the chance of resentment. Assign everyone a meal to take charge of or a day it’s their turn to plan an activity.
If you’re typically the person who deals with the majority of the tasking, I challenge you to relinquish some control. Let your fellow travelers get more invested in the experience. At best, you’ll enjoy just being along for the ride without the pressure of taking care of everything. At worst, your compadres will appreciate all that hard work you do!