Adventure How to Plan an Awesome Group Adventure

by Paola Singer | January 09, 2019

Heading out on an adventure with a band of friends, family or even colleagues can be among life’s most rewarding experiences.

And, with some upfront planning and expert tips, you can take ensure a smooth and memorable journey for you and your crew. Read on to learn more about planning — and enjoying — a group adventure.

Destination is key

Your rendezvous point sets the tone. If your group prefers a degree of independence, opt for a walkable city like San Francisco, New York, Chicago or Portland, where you can all follow your separate muses once the planned outings are done for the day. Pick a centrally located spot for lodging with coffee shops and restaurants in reach so people don't have to rely on the group (or the group's planner) to make every move. 

And, with some upfront planning and expert tips, you can ensure a smooth and memorable journey for you and your crew. Read on to learn more about planning — and enjoying — a group adventure.

If your crew is tight-knit with unified interests, you can pick a more secluded locale. “Italy is one of the top choices for group trips lately,” says Michelle Rago, a destination event planner. “It really has it all, from relaxed beaches to thriving cities, not to mention hundreds of years of history, great food and good service.” She notes that Spain and Portugal are also currently in high demand.

For cross-generational trips, Rago also recommends guest ranches in Montana or Colorado, where families stay close together, but have the freedom pursue activities such as horseback riding, kayaking or trout fishing. And while the turquoise shores of a Caribbean resort spell “vacation” for many, Rago cautions that unless small kids are involved, there are fewer things to do. 

The ultimate challenge, however, is planning a road trip. A few summers ago, parenting blogger Yashy Murphy drove from Dublin to the shores of southwestern Ireland with her husband, a toddler, 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," she recalls. Ireland was an excellent choice, because of the relatively short distances between stops, and the diversity of beautiful landscapes and historic sights.

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Pick a centrally located spot for lodging with coffee shops and restaurants in reach.
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Streamline and simplify

“Avoid connecting flights at all costs — especially if there are children or older people,” advises Eli Ashear, a travel agent with Artisanal Experiences. Ashear recently worked with a client who organized a birthday party in an exotic locale, only to learn his father was hesitating to attend because of a layover.

If a connection is unavoidable or if the group isn’t traveling together, consider hiring VIP ushers. Many large airports around the world — including Newark and LAX — offer meet-and-greet services through third parties like Gateway VIP Services, which can facilitate connections, arrivals and security lines. Other airports — Heathrow in London, for example — have their own concierges.

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

Choose the right lodging

Booking everyone into a cozy boutique hotel is always a good option, because there's generally a sense of intimacy and the service can be more personal. But if there are different budgets within the group, look into a larger hotel. Most major chains allow travelers to reserve rooms at a discount when booking 10 or more. Head to Hotelplanner.com to get competing quotes from thousands of affiliated hotels. If your group is not big enough to qualify for these discounts, it's worth giving the individual property a call. Managers can often set their own rates and might be open to offering perks. Parents should consider seeking out properties with kids’ activities and babysitting services.

For groups of fewer than 10, booking through services like Airbnb or VRBO might make sense. This is good for those who enjoy the budget-friendly option of home-cooked meals. But even larger groups can find the perfect match in a private residence. When Sophie Friedman, a writer from New York, was tasked with finding accommodations in Bordeaux for her group — 17 friends attending a wedding nearby — she snagged a gorgeous and surprisingly affordable 17th-century chateau through Airbnb. "A lot of us hadn't seen each other in years, so we relished the opportunity to share every meal together. It's also really hard to find a table for 17 people in Europe."

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If there are different budgets within the group, look into a larger hotel.
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Be a (benevolent) leader

Don't be afraid to take charge but do make 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 always creates a folder or presentation with images about the destination. "Providing visuals gives everyone a better idea of what the experience might look and feel like."

If leading the charge alone is ultimately too much, assign specific tasks — such as finding a hotel or renting vehicles — to other travelers. You could also assign fellow travelers a day that they plan a dinner or an outing so it's not all on you. Just make sure there’s a command center.

Technology is your friend

Start with Doodle Poll, an app that helps groups settle on a suitable date for all. Sygic Travel Maps, a global app that displays top sights, museums, restaurants, shops and more, sourced from travel editors and fellow travelers, is a nice tool for creating itineraries. Among other useful features, GrupTrip allows users to create a shareable photo album. Splitwise keeps a running tab of who owes money to whom, with an option to settle the bills at the end of the trip, and Travefy aims to be a one-stop shop, serving as an interface for groups to share ideas, itineraries and bills.

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

Hire a travel agent — or learn to think like one

Not everyone has the bandwidth (or patience) to manage the schedules and needs of a group. Not to worry, you can always enlist a professional. Working with a travel agent carries a cost, but a pro could save you money and time. Agents can help negotiate cancellation policies with hotels or quickly rebook a canceled flight — which frees you up to focus on those you're traveling with.

Of course, with so many options to book nearly everything online, learn to think like a travel-planning pro and always ask about additional perks. For example, if you’re traveling with 10 or more people, most airlines offer group discounts and special services like priority check-in. And, to help cover changes in dates or itineraries — the probability of unforeseen events goes up when several people are involved — consider purchasing refundable tickets and group travel insurance.

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Working with a travel agent carries a cost, but a pro could save you money and time.
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A little advance planning goes a long way. Book that larger rental car or van at the airport ahead of time. Reserve your tickets to a museum or sight-seeing activity before you arrive — you might even score a discount. Secure that big table for 15 at the au courant restaurant weeks ahead so you can relax and raise a glass to your truly awesome group adventure.

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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.