Travel Experts Share How To Plan a Group Vacation Without All the Drama

Few things spark dread in me as much as an invitation to join a group vacation. At 29 years old, the idea of going on another alcohol-fueled girl’s trip to Nashville or coordinating a “relaxing” couples getaway in the mountains is about as enticing to me as my annual pap smear. The last time I traveled as a group was this past April, where eight adults rented a villa in Anguilla (say that three times fast.) The clash of personalities, passive aggressive group chats, confusing financial spreadsheets, and stress of trying to please everyone all at once was enough to make me and my partner swear off group travel for good.

While traveling can be an excellent way to build connections and make lifelong friends, it can often be strenuous on relationships, too—especially when you’re stuck with the wrong travel buddies. A 2022 survey sponsored by Exodus Travels found that 69 percent of travelers say the right companion can make or break a trip. This is why many people, like me, narrow it down to a select few people, like partners or siblings. Other people hate group travel so much they simply fly solo. In a 2021 survey of more than 2,300 independent travelers, an average of 56 percent said the reason they go alone is because they want to do what they want, when they want, without anyone holding them back.

This raises an interesting question: Can traveling as a group not suck? At some point in the future I’m going to have to put on my big-girl pants and attend a friend’s bachelorette weekend or milestone birthday in Miami or Vegas. When the time comes, how do we avoid arguing over which restaurants to go to, or who’s footing the bill at the end of our meal?

Kat Jamieson, blogger and founder of the travel app, With Love From Kat, says it all comes down to planning and setting expectations. “The best thing everyone on a group trip can do is be on the same page about finances prior to leaving,” she says. Meals, tickets, toilet paper for the house—it all needs to be accounted for ahead of time, and documented thoroughly during the trip, so there’s no confusion when it’s time to cash out. “It’s better to be overly detailed prior to everyone leaving so there aren’t any surprises.”

But, I know from experience, it’s not that simple. Despite a running tab on Splitwise, the group vacation is an unpredictable beast. Here are the top tips for avoiding trouble in paradise, and how to handle it when it arises.

Expert tips for planning a *good* group vacation

1. Choose your travel companions wisely

Your adventure buddy (or buddies) are unanimously the most important piece of the group vacation puzzle, so say all of the experts interviewed for this piece. “So much of it comes down to who you travel with and what they want to get out of the trip,” says Mike Parker, general manager of trips at Atlas Obscura. “I’ve got dear friends who I think would drive me mad if we had to spend a week straight on the road together, and some of the best co-travelers I’ve ever had are people I hardly knew before taking off.”

The solution, Parker says, is picking people who have similar travel interests as you. If you’re someone who wants to bop around from hostel to hostel, don’t invite the person who prefers luxury, 5-star resorts. Similarly, if you’re the type of person who wants to splurge on fancy drinks and Michelin-star restaurants, find a travel companion who can afford to do these things with you. “Know what you want out of a trip and find co-travelers who share your interests,” he says.

2. Set a budget

Alex Simon, the CEO and co-founder of the budget-based travel app Elude, says that finances are one of the biggest sources of conflict on vacation. “Different incomes, spending preferences, and vacation styles in groups can translate to conflict over spending money on accommodations, excursions, and even meals,” he says. “Finances will always be the elephant in the room, but in order to execute a group vacation, it is important to have a clear understanding of everyone’s budgets and boundaries, as well as set your own.”

Once you gauge everyone’s budgets, it is even more crucial to stick to them. “A good rule of the thumb is to make the person with the lowest budget of the group feel comfortable with the travel plans,” he says. Noted.

3. Build in free time (or set the expectation of a loose itinerary)

Fun fact, folks: You don’t have to do everything together, even if y’all showed up to the same spot. Ravi Roth, LGBTQI+ travel expert and host of Ravi Round the World on Youtube, suggests that everybody get comfortable with a loose itinerary. “Be open to the group splitting up,” Roth says. “People travel for different reasons. One person in your group may thrive with Instagrammable photo opportunities, while someone else may just want to read by the pool. Folks clash when folks do not communicate. I suggest having a talk before a potential trip and each person communicate what they want to do.”

Don’t get offended that your friends want to read by the pool—just let them read by the pool. And plan for this ahead of time, with things like multiple rental vehicles or access to public transportation, so you can successfully and safely split up.

4. Communicate, then communicate some more

Again, things are less likely to go awry if everyone knows what the expectations are before hand. Talk to your group members prior to departure to discuss itinerary planning, dinner reservations, how expenses will be paid, and other logistics. “If cards are all out on the table pre-trip then you will likely all be on the same page,” Roth says.

That said, don’t be a bulldozer, either. There’s a fine line between running point on logistics and abruptly steamrolling what everyone else in the group wants to do. It is, after all, a group trip, so listen to your travel companions’ opinions. “As long as everyone is included in decision-making, they will feel more included and conflict is less likely to happen,” Jamieson says. “Open communication and dialogue is key!”

5. Be adaptable

When is the last time you went on a totally perfect, completely stress-free vacation where nothing went wrong? The answer is never, right? Because stuff happens. Flights get cancelled, credit cards get frozen, bad weather rolls in, and plans change. Don’t be the drama. Just roll with the punches.

“Oftentimes, things come up on a trip and someone may want to veer in a different direction,” Roth says. “Be willing to be adaptable with the itinerary and not stuck in your own way.” And when more large scale itinerary changes do pop up (which can happen), go with the flow. And travel with people who can do the same.

“The best people to travel with are your friends or family that are willing to compromise,” says Simon. “You are never going to find a group of people who want to do exactly the same thing. Therefore, the best qualities to look for [are] someone who is flexible and is happy and excited to adhere to all preferences and make the experience enjoyable for everyone.”

6. Leave the planning to someone else

If you really can’t decide on a travel companion, but want to meet people who are interested in the same cultural experiences you are, join an organized tour. “Just knowing you’ll be with people who have a similar approach and are up for a bit of adventure makes a big difference,” Parker says. “If someone else is setting everything up, there’s less to negotiate with your co-travelers and less to figure out on the fly.”

A quick Google search will serve up hundreds of organized travel tours you can join based on a myriad of different demographics and travel preferences. Some tours, like Eldertreks (ages 50+) and Contiki (18-35) plan tours based on age. Groups like WiFi Tribe and Remote Year host professionals who can work remotely. Companies like Atlas Obscura, Wild Women Expeditions, and Intrepid Travels plan their tours by themes.

“Focusing on a theme can help,” Parker says. “[For example] we offer some incredible food trips that dive really deeply into the culinary scenes of places like Lisbon and Oaxaca. Not everyone wants to spend a week eating adventurously, hanging out with people in the local food scene. If you join a trip like that, you can be pretty sure that your co-travelers are going to want the same kind of experience you do.”

And if conflict does arise…

• Rely on your resources: Can’t decide between snorkeling and a sunset cruise? Sushi restaurant or a steakhouse? Ask a local, your host, or your hotel to weigh in. “If you’re staying in a hotel with a concierge, they can provide a myriad of vetted suggestions for the area, as well as local treasures and hotspots, ” Simon says as an example. “These tend to always be a hit, as people are eager to learn more about the culture of the places they are visiting.”
• Take a beat: All of the experts agree the best thing you can do when your group starts getting ornery is take a break from each other. “Sometimes travel can bring out a different side of someone,” Roth says. “Stress levels can be high. Comfort levels can be exhausted. Take a beat.” Go for a walk, relax by the pool, meditate for 15 minutes—give yourself some time to cool off and reflect before reacting.
• Talk it out: Parker says that if there’s a disagreement, a five-hour car ride in close quarters or on the plane ride back to your hometown probably aren’t the places to commiserate. Neither is the group chat (things can get convoluted quickly). “If you’re hanging out in a beautiful hotel at the end of the day with nothing left on the agenda, it can take a lot of the pressure off of a tense conversation,” he says. “Talk it out in a low-pressure setting.”