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 too trendy) 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 2020.
With Your Influencer Friend: 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.
Or, look at it this way—you get an amazing trip where you can totally unplug from your phone because you know your friend will handle taking all the photos anyway. —Sharell Cook
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. —Wendy Altschuler
With Your Friend Who’s Been Everywhere: Alaska
For the "been there, done that" friend, head to Alaska for a trip that offers new adventures for everyone. There’s a reason it’s called the “Last Frontier"—it's a wild and untamed destination that will leave even the most well-traveled of your friends awestruck. Larger than the states of Texas, California, and Montana combined, this giant piece of land offers breathtaking adventures that can only be had in very few places in the world. Any experienced traveler who thinks they’ve seen it all will quickly think again after catching a glimpse of the astonishing Northern Lights, flying high over the Mendenhall Glacier, riding a seaplane above misty fjords, trekking Denali National Park, or getting up close and personal with humpback whales in Juneau. Never seen a bear or moose up close? It's downright difficult to leave this state without encountering more than a few. Culture vultures who want a taste of the local flavor shouldn’t skip Ketchikan’s Totem Bight State National Park, a celebration of native art in one of the few states where Native American culture still thrives. —Astrid Taran
With Your Friend Who’s a Homebody: Outer Banks, North Carolina
AddressOuter Banks, Kinnakeet, NC, USA
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. —Taylor McIntyre
With Your Foodie Friend: Houston
If eating delicious food throughout your trip is a priority for your group (or just the food snob of the bunch), it’s tough to find a tastier spot than Houston. From pho to food trucks to fusion cuisine, Houston offers foodies a host of opportunities to indulge and imbibe. Take your friends on a Tex-Mex tour of the city. Eat your way through the Heights or Midtown.
Or, if food isn't everyone's top priority, but you need to at least one cool food experience to satisfy that friend, just hit up UB Preserv, the latest creation of local chef Chris Shepherd. The restaurant serves up dishes inspired by several of the city’s most popular eateries, so not only will you get a taste of the city, but you'll experience a sampling of Houston’s cultural and culinary diversity—a win for everyone in the group. —Robyn Correll
With Your Wellness-Obsessed Friend: Isla Holbox
AddressIsla Holbox, Quintana Roo, Mexico
If you're planning a trip with your wellness-obsessed friend—you know, the one whose idea of vacation is waking up at dawn for a sunrise meditation on the beach, followed by an energizing green smoothie before a vinyasa session on the beach—head to Isla Holbox, a quiet island escape located just off the northern tip of Mexico's Yucatan Peninsula. It's a more secluded option than most of Mexico's other more popular beaches, so you can all truly unplug to relax. And while she's up early to perfect her crow pose, the rest of you can sleep in and stroll to the beach later in the day. Plus, there's plenty of activities for you all to do together, such as exploring the island on bicycle (it's the easiest way to get around), swimming with majestic whale sharks who migrate to the warm waters of the Mexican Caribbean between June and September, or paddling a kayak through mangroves while catching glimpses of local wildlife. Then, end your day with a soothing traditional Mayan spa treatment. —Suzanne Barbezat
With Your Friend Who Doesn’t Have a Passport: Hawaii
If someone in your group doesn't own a passport (or forgot to renew it in time for the week you all blocked off for your trip—oops), you'll have to stay domestic for your getaway. Fortunately, you can still enjoy a far-away escape, an unparalleled climate, and a considerable change of scenery without having to leave the country at all. Hawaii’s culture is one-of-a-kind thanks to the customs and cuisine passed down for generations—there is truly no other place in the U.S. quite like this unique archipelago. It’s only a five- to six-hour flight from the closest state, so you can hop on a plane from the mainland in the morning and be sitting on a white sandy beach by the afternoon without waiting in a long customs line. Visit an active volcano on Big Island or hike to a waterfall through the rainforests of Kauai. Enjoy the lively nightlife on Oahu or snorkel with sea turtles on Maui. No matter which island you’re on, Hawaii is bound to scratch that travel itch, no passport required. —Katherine Gallagher
With Your Friends Who Love Road Trips: Southwest US
For those "It's about the journey, not the destination" types, a road trip is the perfect vacation. If long stretches on the road aren't your ideal trip, compromise by choosing an itinerary where you won't be stuck in the car too long. The Southwestern United States offers some of the best road tripping in the country with sprawling deserts between multiple cities and national parks (i.e. plenty of stops along the way). Hit the road in bustling Phoenix, and work your way to the Grand Canyon (Stay at the South Rim, the true “Grand Canyon.") Spend a day in Monument Valley, taking a sunrise tour before heading towards Horseshoe Bend and Antelope Canyon. Then venture to Bryce Canyon and Zion National Parks on your way to your final stop in Sin City itself. You'll experience stunning scenery the whole way, and with all these stops, you're never on the road for more than 3.5 hours at a time. —Melissa Popp
With Your Friends Who Won’t Drive: New York City
For every group of friends that loves a road trip, there’s another whose worst nightmare is spending hours crammed together in a car just to get to the destination. Spare yourselves the “Are we there yet?” complaints, and book a flight to New York City. Few places in the U.S. have as extensive of a public transit system as the Big Apple, so you can spend your entire trip there without ever having to get behind the wheel. All three of the city’s airports are accessible via public transportation, so as soon as you land, you can hop on a bus or a train (or combo of the two) to get wherever you need to go. And practically all of the top attractions are reachable from the extensive public transit system. Take the subway to the Empire State Building, Rockefeller Center, Central Park, the Met, Yankee Stadium, and more. On a nice day, take the Staten Island Ferry to get spectacular (and free) views of the Statue of Liberty and the skyline. After your day of exploring, take the subway back to your hotel even if that’s at 4 a.m.—it runs all night, meaning you always have a ride home. By the end of the trip, you’ll have experienced the best the city has to offer and also have saved yourself the costs of rental car and parking, and the headache of traffic and your friends whining from the back seat. —Jamie Hergenrader
With Your Friends on a Budget: St. Louis
If someone in the group has little to no wiggle room in their budget for a vacation, choose a destination where there's plenty of things to see and do for a low price tag. Our suggestion: St. Louis. Nature lovers could feasibly spend days exploring Forest Park, which covers more than 1,300 acres and is home to the Saint Louis Zoo, Art Museum, History Museum, and Science Center, all of which have free admission. In fact, most of the Gateway City’s museums are free to enter. You can also take a walk along the Delmar Loop and check out the St. Louis Walk of Fame while stopping in some of the shops to browse their wares before grabbing a meal at Salt + Smoke or the eclectic but iconic Blueberry Hill. And you can’t leave the city without getting an up-close look (and photo) of the Gateway Arch (also for free!). With plenty of free attractions and delicious restaurants for all price points, St. Louis is a the perfect choice for planning a budget-friendly trip. —Sherri Gardner
With Your Adventure-ish Friends: New Zealand
If you and your buds are craving some quality time in the great outdoors with some soft adventure, consider New Zealand. By "soft" we mean, you prefer glamping to camping, you'd swap a five-day trek for a five-mile hike, and there's no way you're going to fling yourself out of a plane or off a bridge.
Even through the country is well known for its adrenaline-inducing activities like bungee jumping and skydiving, there are plenty of amazing things to do for those who prefer to keep their feet firmly on the ground. For instance, New Zealand is home to some of the best hiking on the planet that will suit all levels of explorers; its seemingly endless coastline offers great paddling and also the experience of cycling between coastal vineyards; and at the end of the day, you can indulge with some local wine (maybe a bottle that you picked up on your cycling excursion), unplug in a remote eco-lodge, and relax in a hot spring or geothermal mud bath. And if you are one of those people who does want to cross bungee jumping in New Zealand off your bucket list, go for it, and then you can tell your adventure-ish friends all about it when you get back. —Kraig Becker
With Your Friend Who Needs to Let Loose: Miami
Miami is the perfect destination for that friend who really needs to escape work, a recent breakup, or whatever else might be plaguing the good vibes on your trip. The city's nightlife and party scene is unlike any other city in the U.S., but it also offers plenty of daytime options to help you unwind. Check in at the Standard, Miami Beach and book a spa treatment or grab a cocktail by the pool at Lido Bayside Grille. While there, you can also participate in the establishment's new moon meditations as well as sunset stand-up paddleboarding. Or get your fill of sightseeing on Ocean Drive by taking a walking tour of the district, renting bikes to explore, grabbing a bite to eat at one of the stretch's iconic restaurants.
Once you've done your daytime relaxing, it's time to recharge with the city's thriving nightlife. Many of the bars and clubs stay open until 5 a.m., but that won't be a problem because the next morning, you'll be ready to start all over again with a relaxing day by the pool. —Allison Ramirez