How to Organize a Stress-Free Trip with Your Friends

Traveling with friends is an art. When done right, it leads to amazing times filled with exciting adventures, well-crafted Spotify playlists, and lots of laughter. When done wrong, it can turn into a stressful situation full of tension and drama. No one wants that.
Fortunately, you can sidestep these pitfalls while planning your next “friendcation.” I consulted numerous experts and seasoned travelers, combined with my own experiences journeying around the globe with friends, to bring you this guide.

Consider this your comprehensive guide to enjoying group travel—without the headaches.

Designate a leader

Anyone who's traveled in a large group knows that someone will inevitably step up to take charge. I can’t stress this enough: Embrace this dynamic. “Having a leader or even a small committee of two to three people makes everything easier,” confirms Michael Brein, PhD, a travel psychologist. To understate it: It significantly streamlines the process.

Evaluate Your Group's Dynamics

In an ideal world, we would always get to choose our travel companions. Fun Bobby? Absolutely! Fun Bobby’s irritating best friend? No thanks. However, the reality is that you often have to invite that annoying friend along. Brein suggests adopting a psychologist's mindset to ensure everyone has a good time.

Here are a few questions to consider:

• Is everyone in the group aligned on how they want to spend their time?
• Do most prefer relaxing at home or going out to clubs?
• Are group members more cautious or adventurous?
• How do introverts and extroverts balance in the group?

Brein advises taking note of these personality traits within your group to help create an itinerary that caters to everyone’s preferences.

Seek Out Group Discounts

One of the major advantages of traveling with a (friendly) pack is the potential for great deals. Tim Hentschel, cofounder and CEO of Hotelplanner.com, notes that “if you’re traveling with 10 or more people, you qualify for group airfare rates, which can help you negotiate perks like waiving change fees or even swapping passenger names.” This means you could potentially replace a friend who can't make it last minute with someone else at no extra cost.

You can also snag great group deals on accommodations. “Many hotels will provide a complimentary suite upgrade for bookings of more than 10 rooms. Don’t hesitate to ask if it’s not offered,” advises Hentschel. He also recommends planning at least one group meal or cocktail gathering at the hotel. “If you arrange something through the catering department rather than just heading to the bar, you’ll be placed on the hotel’s group VIP list, giving you higher priority.” In addition to hotel perks, group rentals are another fantastic option. For a more luxurious experience, consider upscale home rental sites like onefinestay and Oasis, along with the usual platforms like Airbnb and Vrbo. If accommodations vary in quality, reserve the best room for your fearless leader as a thank-you for their hard work.

Utilize Google Drive and Apps for Organization

While it might feel a bit tedious to bring office skills into your vacation, group travel often requires it. As travel writer and expert trip planner Sophie Friedman puts it, “Google Docs and Google Sheets are essential—especially since everyone can edit them to add their needs or desired activities.”

There are also (free) apps to assist with this.

• Travefy: This app allows you to compile everyone’s flight and hotel details into a single, shareable itinerary, plus you can chat with fellow travelers directly in the app. It also includes group polling for easy decision-making.
• Troupe: Introduced by JetBlue in 2022, this app is great for groups collaborating on an itinerary, featuring a dedicated chat function (including threads) for suggesting activities, sharing links and videos, and providing feedback. Like Travefy, you can also vote on options and even book accommodations through the app.
• Doodle: If you’re focused solely on creating group polls, this is the app for you. It’s available on desktop as well, allowing you to send Doodle polls via email.

Apps can also assist with the inevitable money management issue. Is there anything worse than enjoying a fantastic trip with friends, only to face the daunting task of figuring out who owes what at the end? Fortunately, Travefy includes group financial features (unlike Troupe), but there are other free apps that can help as well:

• Splitwise: Each person inputs their expenses, and Splitwise calculates who owes what. With its partnerships with Venmo and PayPal, you can pay directly through the app. However, it doesn’t support international currencies, so if you’re traveling abroad, consider upgrading to Splitwise Pro for $4.99 a month, which includes currency conversion and receipt scanning features.
• Tricount: This app does handle currency conversion but lacks Venmo or PayPal integration, meaning you'll need to settle up with friends outside the app. No account creation is required, making it simpler to use than Splitwise.

Plan Your Meals

A significant portion of your budget will go toward food and drinks, so it's wise to strategize.
If you're staying at a hotel, expect to dine out often, so remember to make restaurant reservations ahead of time (and take advantage of group-rate dining as suggested by Hentschel). If you choose a rental, you can prepare large, enjoyable group meals—something Yasmin Fahr, a cookbook author based in Menorca, appreciates about vacation rentals. “Cooking enhances the experience. You can mix drinks, chop veggies together, and enjoy each other's company. Food really brings people together,” she notes.

Cooking for a large group can be more challenging than it seems. Fahr suggests making an initial grocery run for essentials—like eggs, bread, jam, and cheese—then sourcing local ingredients for the rest. “During a group trip to Deauville, France, we discovered an amazing farmers’ market where we bought fresh scallops and prawns. We ended up making cioppino, a tomato-based fish stew, served with some crusty local bread. It was such a blast to utilize local produce and create something special,” she recalls.

Fahr also recommends summer tacos, which cater to everyone’s tastes, including those with dietary restrictions, and a hearty roast with plenty of veggie sides for winter gatherings. “Both options foster a communal dining experience that brings everyone together,” she notes.

Now that you have the tools for a stress-free trip, you can savor that quality time with friends even more. In our fast-paced digital world, those rare moments of genuine connection are invaluable. Ultimately, that’s what traveling with friends is all about.

This article was first published in June 2018 and updated with new insights in September 2024.