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How to Plan an Unforgettable Group Trip

by Paola Singer |June 6, 2023

Traveling with a bunch of friends or family can be among life's most rewarding experiences, especially when you put time and thought into the pre-trip planning.

To help you make smart decisions on your destination, activities, lodging and more, we tapped top pros for their best group-travel tips. These expert ideas can help you get organized, enjoy the journey and ensure it all happens without a hitch.

a group of friends celebrate with their hands in the air at the top of a mountain

Consider personalities

Your choice of destination will have a big impact on the experience, so think carefully about which setting will suit your group best. If your companions are the type who like their independence, for example, you may want a walkable city like San Francisco, New York, Chicago or Portland, where you can all go your own way once the planned outings are done for the day. For lodging, pick a centrally located spot with easy access to coffee shops and restaurants; that way, everyone can easily find what they need without having to rely on the group.

If, instead, you're a tight-knit crew with unified interests, you might try a more secluded locale, suggests destination event planner Michelle Rago. (Think a small beach town in Portugal or a historic village in Italy.)

For cross-generational trips, guest ranches in Montana or Colorado are an ideal option, Rago adds, because families can stay close together and also have the freedom to do activities like horseback riding, kayaking or trout fishing on their own.

A road trip abroad can also be a crowd-pleaser — even if participants have different interests and sleep habits, according to parenting blogger Yashy Murphy, who once drove from Dublin to the shores of southwestern Ireland with her husband, their child, her in-laws and two aunts. "Some people liked to sleep in, while others were early risers, so I made sure to plan morning activities and come back in time for lunch to meet the rest of the group," Murphy says. Ireland was an excellent choice, she adds, because of the relatively short distances between stops and the diversity of beautiful landscapes and historic sights.

A family with 2 kids sit on the ground looking out at mountain scenery

Stay organized, from start to finish

Online tools and apps can streamline your planning. Instead of trying to pick a date over an unwieldly group chat or email chain, for example, send out a poll via, a free scheduler that can automatically pinpoint the group's preferred options. Sygic Travel Maps, a global app that compiles top sights, museums, restaurants, shops and more from travel editors and fellow travelers, is a helpful tool for creating itineraries. And the Splitwise app is an easy way to keep a running tab of who owes money to whom, with an option to settle the bills at the end of the trip.

Choose transportation strategically

The more people you have on your trip, the more of a possibility there is for unexpected snafus like missed flights or lost luggage. Your best bet is to keep the travel plans as streamlined as possible. "Avoid connecting flights at all costs, especially if there are children or older people," advises Eli Ashear, a travel agent with Embark Beyond, because those can add a layer of unnecessary stress. (Ashear once worked with a client who organized a birthday party in an exotic locale, only to learn his father was hesitating to attend because it entailed a layover, he says.)

If a connection is the only way to get there, consider hiring VIP ushers. For an added fee, many large airports around the world offer concierges or meet-and-greet services through third parties that can facilitate connections, arrivals and getting through security lines.

Four friends look out upon the New York City skyline

Get the most out of your lodging

You want everyone to be comfortable and happy with where you're staying, so understanding the group's expectations and budget is a good place to start to help you narrow down your options. A cozy boutique hotel is often a good choice for a group because there's generally a sense of intimacy and the service can be more personal. But if your companions' price ranges vary, a larger hotel can be an easier option because many major chains allow travelers to reserve rooms at a discount when booking 10 or more. Even if your crew is not quite big enough to qualify, it's a good idea to call the property to inquire about a special rate or potential perks.

Be a (benevolent) leader

If you're the one in charge, make an effort to be sure every traveler feels included and heard. "The person doing the planning should try to curate all the possibilities for the trip, thinking about different types of activities and even options for downtime, and then share [the plan] with the rest for feedback," says Rago. She also suggests creating a folder or presentation of the destination and potential plans with images. "Providing visuals gives everyone a better idea of what the experience might look and feel like," Rago says.

If you find that leading the charge alone is too much, you may want to assign other travelers specific tasks, such as finding a hotel, making dinner or renting vehicles.

Hire a travel agent — or think like one

Not everyone has the bandwidth (or patience) to manage the schedules and needs of a group, so it can be helpful to enlist a professional. Working with a travel agent carries a cost, but a pro could also end up saving you money and time. Agents can help negotiate cancellation policies with hotels or quickly rebook a canceled flight, freeing you up to focus on those you're traveling with, for example.

Of course, you can also tackle these types of tasks on your own; if you're traveling with 10 or more people, many airlines offer group discounts and special services like priority check-in, so all you'll need to do is ask. You can also protect against fees for changes in dates or itineraries by purchasing refundable tickets and group travel insurance.

— With additional reporting from Life and Money by Citi editors.

Paola Singer

is a Manhattan-based writer who covers food, travel and design. Her stories have been published in The New York Times, Architectural Digest and Conde Nast Traveler.

The content reflects the view of the author of the article and does not necessarily reflect the views of Citi or its employees, and we do not guarantee the accuracy or completeness of the information presented in the article.