How to Plan a Friend Trip

Whoever said a friend is a friend forever has clearly never experienced a group trip that has devolved into a maelstrom of conflicting plans and bickering over restaurant bills. Traveling with your besties can be tricky. Here are some ways to do it without anyone getting unfriended.

“First and foremost, you cannot travel with everybody. All your friends are not travel friends,” advises N’dea Irvin-Choy, a 27-year-old Los Angeles-based travel influencer, on her popular TikTok account. She suggests picking travel partners who share similar interests, and deciding ahead of time what kind of a trip you will be taking — relaxation, partying, adventure. “The last thing you want is for your friends to be giving each other the silent treatment on a nonrefundable excursion somewhere on a beautiful tropical island,” she explained in an email.

You can get the ball rolling by asking your friends where they want to go and what they want to do using services like Doodle, Google Forms and Troupe. Some people prefer to use familiar spreadsheet programs like Microsoft Excel or Google Sheets to organize the plan and share it with friends. Others prefer to use apps like Hoku, MiTravel and Plan Harmony that allow group members to collaborate in the planning process with photos, maps and more. And creating an Airbnb wish list lets friends suggest lodging options for the whole group to see. Once you’re in booking mode, Mobili provides a way to see each group member’s travel bookings at once, a tool that is especially useful for larger groups.

For sorting out flight arrangements, Robert Driscoll, who owns the L.G.B.T.Q.-focused travel agency VentureOut, swears by TripIt. After making your bookings, you can forward your confirmation emails to the app, which puts them all together on one timeline. Others in the group can then collaborate with the same trip by adding their own bookings to create a group itinerary. “It’s basically a chronological compilation of all your arrangements: flights, accommodations, car rentals, restaurants, activities, tours,” he said.

When one participant on a friend trip suddenly drops out, it can throw financing for the whole trip into disarray. Hedge against those monkey wrenches by setting a firm deadline for a monetary commitment. When people put down real money, whether for lodging or activities, they’re more likely to follow through.

Use a classic schoolteacher’s trick to keep everyone engaged and share the planning burden: Schedule a rotating group leader to take ownership of each day’s activities. This person will be responsible for making that day’s restaurant and tour reservations, or simply keeping everyone on schedule. Ask each friend to share a personal desire for the trip — for example, a tour of a museum or an afternoon at the beach — and assign that person to lead the group on the day of that activity. By making everyone the driver, everyone also gets the chance at some point to sit back and be a passenger.

Tracking expenses for a whole group can expose a lot of pain points. Differing price sensitivities and priorities make things complicated enough, and that’s before you get into the challenges of pricing couples versus singles, people who join late or stay longer, or charges in multiple currencies. “I have seen so many friendships dissolve because resentment builds when one person suspects other friends are taking advantage of her financially, or not pulling their weight,” said the friendship coach Danielle Bayard Jackson, who is based in Tampa, Fla.

Apps can help make complicated calculations easy and transparent, even while the trip is still underway. Mrs. Jackson said she liked TravelSpend, which automatically converts currencies, and Splitwise, which integrates with Venmo, to “help groups manage everyone’s tabs so there’s no confusion about who owes what.” For divvying up restaurant bills, Ms. Irvin-Choy said she recommended the app Tab, which uses a picture of the receipt to track each diner’s responsibility.

Groups can easily become what Dina Vaccari, a Seattle-based traveler, calls the travel amoeba: “an excruciatingly slow-moving blob of people that doesn’t really get anywhere.” There are countless situations where the group may end up stalled — when one member runs back to grab a lost hat or needs to use the bathroom or stop at an A.T.M. Decide as a group ahead of time that it’s OK not to wait and set a time and a place to meet up again. Or use the location-sharing feature of apps like WhatsApp, so that stragglers can catch up on their own schedules and the rest of the group is free to keep exploring.

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