How to Plan the Perfect Group Trip (Without the Stress)

Traveling with your friends is a true art form. Done well, it can be the most glorious of times, filled with casual day drinking, perfectly curated Spotify playlists, and tons of laughter. Done poorly, it can get bad. Tension-filled, he-said-she-said bad. No one wants that.

But you can avoid that fate as we head into summer, aka the season of “friendcations.” I consulted a slew of experts and travelers with plenty of wisdom on group getaways, and together with my own experience traveling all over the world with friends, we’ve got you covered.

Consider this your ultimate guide to traveling with a big group of people—no big headache required.

First things first: Let someone lead.

Anyone who has ever traveled in a large group knows that someone, somewhere, inevitably ends up stepping up to the plate and acting as leader. I cannot emphasize this enough: Do not try to resist this dynamic. “Having a leader or even a small committee of two to three [leaders] maximum makes things much easier for everyone,” confirms Michael Brein, PhD, travel psychologist, and host of The Travel Psychologist Travel Tales podcast. Risking understatement: It streamlines the process big time.

Next up: Assess your group dynamics.  

In a dream world, we would all be able to choose exactly who we travel with at all times. Fun Bobby? Always yes. Fun Bobby’s annoying best friend? Hard pass. But the reality of the situation is that you often have to invite Fun Bobby’s annoying best friend. So Brein suggests you put on your psychologist’s hat and act accordingly.

A couple of questions to ask:

• Are all your group members on the same page about how you like to spend your time?
• Do most people in the group prefer to chill out at home or go hit the clubs?
• Are people more fearful or more adventurous?
• What about introverts and extroverts?

Brein recommends making notes on how your group spreads out across those various personality factors so you can better design an itinerary that addresses everyone’s needs.

Speaking of itineraries, try to go for group rates whenever possible.

One of the biggest perks of traveling with a (friendly) wolf pack is that you can clean up in the deals department. Tim Hentschel, cofounder and CEO of hotelplanner.com, explains that “if you’re flying with 10 or more people, you qualify for group airfare rates, which could help you negotiate perks, like the ability to waive a change fee, or even swap passenger names.” This means that you could theoretically replace a friend who can’t come at the last minute with someone who can—all at no cost.

Photo by Jon Tyson/Unsplash

Layovers are much more bearable when everyone is together.

Hotel perks aside, group rentals are also a great option. If you want to go super luxe, check out some upscale home rental sites, like onefinestay and Oasis, in addition to your usual suspects (Airbnb, VRBO, etc.). If the rooms aren’t equal, give the best one to your fearless leader as a reward for all the hard work.

Use Google Drive and apps to keep things organized.

While it may seem a bit soul crushing to apply your office skills to your vacation, group travel pretty much demands it. Or, as travel writer and group trip–planner extraordinaire Sophie Friedman puts it, “Google Docs and Google spreadsheets are life—especially because everyone can edit them and put in any requirements they have or activities they want to do.”

There are (free) apps for that, too.

• Travefy. It lets you gather everyone’s flight and hotel info into one single, shareable itinerary, and you can chat with everyone on your trip in the app. You can also create group polls, enabling you to easily take a crowd vote.
• Prava. Similarly, you can share a group itinerary and talk to your friends within this app, but Prava has an additional feature that lets you share your location while doing so.
• Doodle. If you only want to create group polls, go for this one. It’s also available in desktop form, which allows you to send a Doodle poll in an email.

Apps can help you with the dreaded money issue, too.

I ask you: Is there anything worse than having an amazing trip with your favorite people, only to realize at the end that you still have to tally everything up and see who owes what? Fortunately, both Travefy and Prava have additional group financial features, but these other apps can also help:

• Splitwise (free). Everyone enters the amount they paid, and Splitwise tells you who owes what. Thanks to a partnership with Venmo, you can settle your bill directly in the app. One problem: Splitwise doesn’t factor in international currencies, so if you’re traveling abroad, consider downloading Splitwise Pro, which costs $2.99 per month but has currency conversion capabilities, as well as other features, like the ability to scan your receipts.
• Splittr ($1.99). It does convert your currency, but it does not incorporate Venmo or payment abilities, so you’ll have to pay your friends back outside of the app.

A lot of your money goes toward food and drinks, so go into your trip thinking about food and drinks.

If you’re staying in a hotel, you’ll probably end up eating out for most meals, so don’t forget to book restaurant reservations in advance (and be sure to do as Hentschel recommends and get in on that group-rate dinner). But if you’re taking the rental route, you can cook up big, fun group meals—which is one of the reasons Yasmin Fahr, food and travel writer and founder of the travel membership club LokaPack, loves the homesharing option. “Cooking adds a nice element to your experience. You make a nice cocktail, chop some vegetables together, and talk. I love how food fosters a sense of community and brings everyone together,” she says.

Photo by oneinchpunch/Shutterstock

Twinkling lights and sparklers are optional but recommended.

Of course, cooking for a large group is easier said than done. Fahr’s advice: Make one grocery run at the beginning of the trip for basic stuff—think eggs, bread and jam, and good cheese, for starters—and then go local for the rest. “When I was in Deauville, France, for a group trip, we went to this incredible farmers’ market and picked up fresh scallops and prawns. Then we made cioppino, a tomato-based fish stew, and paired it with local crusty bread. It was so much fun to use what was from that region and make our own thing out of it,” she recalls.

Fahr’s other go-to dishes for group trips are tacos in the summer—which have something for everyone, even people with dietary restrictions—and a big roast with lots of veggie sides in the winter. “Both are fun, communal meals that bring everyone together,” she says.

And now that you know how to plan a low-stress trip, you’ll be able to enjoy that quality time together even more. In today’s all-too-hectic, digital world, those rare uninterrupted moments of togetherness are precious. And that’s really what traveling with your friends is all about.

>>Next: 10 Must-Read Books for Every Type of Summer Trip