Traveling with a group of friends, even your closest ones, can be challenging. And we’re not talking about the logistics of booking multiple flights or jamming all your luggage into one small car. Most often, choosing the destination can be the most difficult step, since every group seems to have that one friend (or friends) who can make planning a little more of a hassle.

You know that friend—the one who has to travel somewhere that’s trendy (but not tootrendy) and filled with picturesque photo ops for the ‘gram; or the one who forgot to renew his passport in time for the international trip you had discussed; or the couple who’s bringing their kids, making it officially a family-friendly getaway for all. Or maybe you’re the difficult one. Regardless of the challenge that comes with trying to please multiple personalities, you still want to travel somewhere that everyone will enjoy, even—and especially—the most-hard-to-please of the bunch (if they’re happy, everyone’s happy).

In the spirit of spring break season, we’re solving the problem of group travel indecisiveness. We used a mix of data from our Editors’ Choice Awards plus some editorial insight to choose the best spots for group travel this year. Here’s our complete list of the best places to go with your crew in 2019.

With Your Influencer Friend: Sri Lanka

Aerial view on green tea plantation in mountains in Sri Lanka

Sri Lanka has reinvented itself from the ravages of more than two decades of civil war, and it’s on its way to becoming one of world’s trendiest travel destinations—perfect for your friend who always seeks out the coolest new place to go (and the attention that comes with it in the form of Instagram likes).

No longer an underrated country overshadowed by India, it has a fresh new “So Sri Lanka” tourism brand that’s aimed at modern, experience-seeking young travelers. Stay in a hip heritage hotel in Colombo or Galle, ride the historic mountain railway and tour the tea estates in Hill Country, hike through the Sinharaja rain forest, spot herds of elephants at Minneriya or Kaudulla National Parks, glamp in the wild at Yala or Wilpattu national parks, visit ancient temples and go hot air ballooning in the Cultural Triangle, capture the country’s lush landscape from a panoramic peak, surf and party on the beach at Arugam Bay, discover secluded islands off the northern coast near Jaffna, and get an Ayurvedic wellness treatment.

With Your Friends Who Are Bringing Their Kids: Chicago

Imagine this scenario—you’re planning your annual trip with your best pals, and in the midst of planning, they announce they’re bringing their kids this time. Please the parents, the kiddos, and the rest of the group by heading to Chicago where the list of places to go with kids in tow is long.

Topnotch museums like Adler Planetarium, Shedd Aquarium, The Art Institute of Chicago, The Field Museum, Museum of Science and Industry and Museum of Contemporary Art Chicago all have special programming for little ones, so you and the other adults can roam the exhibits kid-free for at least part of the visit.

You can also spend your vacation park-hopping in more than 8,000 acres of public parks—Millennium Park (with Cloud Gate a.k.a. “The Bean”), Grant Park (with Buckingham Fountain), Lincoln Park (with Lincoln Park Zoo, the Lincoln Park Conservatory and the Lincoln Park Cultural Center) and The 606 (green space built on an elevated train track).

For a thrill, book an indoor skydiving flight at iFLY and check out their new virtual reality experience—kids as young as six can fly. Practice your espionage skills at SafeHouse Chicago, a spy-themed bar and restaurant with a magic show and interactive games. Step out onto The Ledge, a glass balcony extending four feet outside of the iconic Willis Tower (or Sears Tower if you’re a local), 103 floors high—you can’t beat the views.

With Your Friend Who’s a Homebody: Outer Banks, North Carolina

If half of your group wants to book a beach getaway while the other half prefers am action-packed itinerary of sightseeing, please both parties with this compromise: Outer Banks, North Carolina. The homebodies of the group can cozy up in an ocean-front cottage overlooking a gorgeous beach from the window, and if they muster up the energy to leave the house, they won’t have to go far to find a secluded beach to continue lounging with a drink and book in hand. Those in the carpe diem camp can keep busy by exploring Jockey’s Ridge State Park (home to the highest sand dunes on the east coast), touring the Cape Hatteras lighthouse, or visiting the North Carolina Aquarium (where you can hold giant horseshoe crab). Both parties might enjoy a trip to the north islands of Corolla where there are more wild horses than there are people. The Outer Banks is a great destination that will please both the beach bums and the go-getters in your group.



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