Troupe featured on Travel Massive

Planning group vacations is far from easy. The group trip planner takes on a huge role in researching, planning, and organizing everything from flight times to airport transportation and accommodations.

But in addition to that, they also have to deal with getting friends to commit to the group vacation in the first place. And once they’re committed, the work doesn’t stop there. When you put a bunch of individuals together, you’re going to have different desires, budgets, and beliefs on what is most important.

To make it easier, we’ve put together the most important conversations to ask before group vacations, to help with planning and to ensure every group member has a great time.

Important conversations to have before group vacations include:

  1. Express any desires before you travel
  2. Remember it isn’t a dictatorship
  3. Stay focused on the point of the trip
  4. Discuss how to split costs
  5. Find a way to involve everyone

Important conversations to have before group vacations

1 Express any desires before the trip

Once the plane touches down at your destination is not the time to have strong opinions on the itinerary of the trip. If there’s a specific museum you’re dying to see or a restaurant you really want to try, communicate these wants in advance of your departure. At least a few other people are likely to want to do the same thing, but you’re also giving everyone the option of opting in/out for any reason by talking about it in advance.

In fact, nearly 50% of travelers we interviewed think a trip is more likely to happen when every person’s opinion is factored in.

2 This isn’t a dictatorship…

…if you don’t feel up for something, don’t feel forced. 

Everyone needs a nap when they need a nap. It’s not a reflection on your commitment to the group if there’s something on the schedule that you just don’t feel up for doing. You can always decide to sit something out. 

This option should be available to everyone, all the time, judgement-free. 

The only consideration should be if there are group activities at your destination which require a pre-commitment to determine costs. If you opted in for something that you don’t feel like doing anymore, you should still pay your fair share.

a girl sits in a hammock alone with greenery in the background on a porch reading a book.
Photo by Radek Grzybowski on Unsplash

3. Stay focused on the point of the trip

Whatever the occasion, always come back to it.

Maintain focus on whatever the trip is about. If you’re celebrating a bride or groom-to-be, find occasions during the trip to get excited with them for the wedding. Let them know they’re supported, calm their fears, and, frankly, do whatever the heck they need. Find moments to make them feel special and loved in whatever way you can. Plan surprises catered to their favorite things. 

Similarly, if you’re just on a girls’/guys’ getaway or a family vacation, it’s nice to find meaningful ways of spending the time together. If you’re drinking, use each ‘cheers’ as a chance to express gratitude for a different person on the trip, or play a “Secret Santa” souvenir game where each person is responsible for buying a nice memento for someone else.  

group vacations palm trees in the background looking up at a group of groomsmen and a groom cheers'ing with beers

4. Discuss how to split costs 

Some people on a group trip may have plenty of money to spare while others are pinching pennies. It can be hard for the ones splurging to remember that things that don’t seem like a big deal or an expensive purchase to them may be causing others in the group financial anxiety. This means it can get very complicated to handle split expenses on a group trip.

At group dinners, be aware of someone ordering a salad, or not drinking alcohol, or otherwise spending significantly less than the rest. Whether they’re doing it on purpose or not, they literally don’t owe as much as the rest and shouldn’t have to keep splitting things equally. 

When we asked travelers if they would be less likely to commit to group vacations if budget was not discussed, nearly 1 out of every 3 people either agreed or strongly agreed.

5. Find a way to involve everyone 

Even if someone thinks they’ll be happy going with the flow on the trip it can be nice for the group organizer to figure out little things to make everyone feel involved.

Finding “categories” can be a great way to delegate this. Ask the group what they’re most interested in when it comes to researching/planning. Options can include accommodations, museums/culture, food, drinks, adventure activities… whatever applies.

This way, you’re utilizing everyone’s individual knowledge and specialties, helping everyone feel involved, and minimizing the responsibilities on the main trip planner.

Alternatively, let each person plan one day or be the one to make decisions on-the-go for one day while you’re there.

girl with a black ponytail, colorful ruffled shirt and white and black floppy hat from behind stands looking at an abstract colorful painting against a white background
Photo by Vincent Tantardini on Unsplash

Having a few simple, but important conversations before you set out on your group vacations will help make the entire experience more enjoyable for everyone. To help you with the planning, check out Troupe’s group travel planner app where you can vote on destinations, share flight details, and much more!


Where can I travel with a group?

Some of the best places to travel with a group in the US are Nashville, Austin, Denver, and Las Vegas. Internationally, group vacations to Colombia, Mexico, and the Dominican Republic are some of the best options.

Where are the best all-inclusive resorts for group trips?

Mexico, the Dominican Republic, and Jamaica have some of the best all-inclusive options for group trips to resorts.