How to Plan a Stress-Free Trip With Your Friends

Traveling with your friends is a true art form. Done well, it can be the most glorious of times, filled with inspired adventures, 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 you plan your next “friendcation.” 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.

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. Risking understatement: It streamlines the process big time.

Assess your group dynamic

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 so everyone enjoys themself.

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 which of those various personality factors your group has so you can better design an itinerary that addresses everyone’s needs.

Look for group rates

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

You can also score sweet group deals on your accommodation. “Most hotels will offer a complimentary suite upgrade if you book more than 10 rooms. Be sure to ask if it’s not offered,” says Hentschel. His other advice: Try to plan at least one group meal or cocktail gathering at the hotel. “If you organize something through the catering department versus just going with a group to the bar, you’ll be added to the hotel’s group VIP list and will be considered a higher priority.” 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, group trip–planner extraordinaire, and Afar contributor 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.
• Troupe: Launched by JetBlue in 2022, this app is best for groups who want to collaborate on an itinerary, with a dedicated chat feature (including discussion threads) that you can use to suggest activities, share links and videos, and give feedback on others’ ideas. Then, like Travefy, you can also vote as a group once all of the options are on the table—and you can even book accommodation directly through the app.
• 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. 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, Travefy has additional group financial features (Troupe does not), but these other free apps can also help:

• Splitwise: Everyone enters the amount they paid, and Splitwise tells you who owes what. Thanks to partnerships with Venmo and PayPal, 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 $4.99 per month but has currency conversion capabilities, as well as other features, like the ability to scan your receipts.
• Tricount: It does convert your currency, but it does not incorporate Venmo or PayPal, so you’ll have to pay your friends or family members back outside of the app. You also don’t need to create an account to use this app, which makes it slightly easier than Splitwise, which requires one.

Plan your meals

A lot of your money goes toward food and drinks, so go into your trip thinking about how you’ll handle both.
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, Menorca-based cookbook author of Cook Simply, Live Fully and New York Times recipe contributor, loves the vacation-rental 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

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—eggs, bread and jam, and 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.

This article was originally published in June 2018 and was updated with new information in September 2024.