Where to Travel With Friends, Every Month of 2026

Life can get busy, but no matter what time of year you and your friends are able to carve out some time to escape, there's an ideal destination waiting. While you certainly don’t need a special occasion to take a trip with your posse—sometimes everyone’s schedules align, or a simple “I’m burned-out; want to get away next weekend?” text in the group chat is reason enough to jet off—celebrating a major life moment is always the perfect excuse. Maybe your bestie just landed a big promotion, ​or perhaps you’re toasting a milestone birthday. Either way, it’s worth packing your bags. Of course, you’ll want to pick a spot that matches the group vibe. That might mean going big on adventure, focusing on food or blocking the bulk of time for leisure and wellness. As the resident planner, you want to satisfy them all and make the trip one to remember.

Because where and when are equally important for a group getaway, it’s essential to also consider the seasonal factors. In January, your trip might include swooshing down the slopes, après-ski antics and spa time in snow-covered Park City, Utah. Come June, the sun-dappled beaches of Portugal’s Comporta call. And the fall foliage in Asheville, North Carolina, guarantees glorious hiking and photo ops in October.

From Anguilla to Tokyo, these friendcation-focused destinations ​ensure a memorable vacation with your crew.

January: Park City, Utah

The firepit, chalet globe and Airstream turned food truck at Montage Deer Valley equate to fun winter hangouts.

A favorite of groups who shred and enjoy a more laid-back après scene than what you’ll find in Aspen, Park City gets an average of 25 feet of snow each season. Come January, the peaks are practically guaranteed to be blanketed in fresh powder, and visitors will find more than 7,300 acres of skiable terrain, plus a modern lift system. Newbies nervous about keeping stride with the group can opt for private lessons—and if everyone needs a break from the downhill action, the small and walkable downtown area is dotted with quaint restaurants (Courchevel Bistro is a favorite for swanky French fare) as well as high-end shops like Kemo Sabe—the chic Aspen export for bespoke cowboy hats—and outerwear retailers. Stay at the slope-side Montage Deer Valley, which features spacious rooms and suites (many of which connect), a heated outdoor pool and excellent spa for post-skiing rest and relaxation, plus firepits for nightly s’mores.

February: Anguilla

When it comes to R&R, what could be better than a seaside spa massage at Cap Juluca, A Belmond Hotel, Anguilla?

The best way to beat the winter blues during the coldest, bleakest month of the year? Escaping to the Caribbean for a just-because-it’s-a-long-weekend trip of swimsuit weather, sun and sand. In Anguilla, high-end resorts cater to the whims of even the fussiest friends. Pals staying at Cap Juluca, A Belmond Hotel, Anguilla can start the day with a beachfront yoga session before digging in to breakfast with wave views. Most of your group’s unstructured time will probably be spent at the beach or by the pool with a fresh-cracked coconut to sip—but if you want to break up the horizontal hang sessions, there’s an excellent spa and an 18-hole Greg Norman–designed golf course overlooking Rendezvous Bay. Anguilla’s dining scene is also one of the best in the Caribbean, with plenty of fine-dining restaurants for dress-up nights as well as some more low-key options for when the group wants to go straight from the beach to dinner. For a crowd-pleasing, no-reservations-required spot to watch the sunset while devouring grilled chicken, ribs and snapper and swigging a cold beer or rum punch, head to the SunShine Shack, over on Rendezvous Beach.

March: Tokyo, Japan

Even after repeat visits, Tokyo’s glimmering skyline can still wow even the most worldly friend.

Japan’s thrilling capital dazzles travelers with neon lights, futuristic skyscrapers, cool fashion and incredible food, making it the perfect destination for that one hard-to-impress friend. March is an especially good time to visit for the chance to spy Kawazu-zakura—early-blooming cherry blossoms—along the Oyoko River, before the tourist crush in April. History buffs can visit Senso-ji, the oldest temple in Tokyo, while gourmands do a self-guided food tour of ramen, sushiOpens overlay and unagi shops in the surrounding Asakusa neighborhood. And fashion lovers will want to explore the districts of Ginza and Omotesando, which supply upscale shopping, from luxury designers to curated vintage stores. Also make time for a stroll through Yoyogi Park before doing the famous Shibuya scramble, the world’s largest pedestrian crossing. Of course, Tokyo has its share of eclectic hotels, but culturally curious pals looking for a modern ryokan experience should check in to HOSHINOYA Tokyo for traditional tatami mat floors, tea lounges and an onsen that’s open to the night sky. For sleek style and some peace and quiet, TRUNK(HOTEL) YOYOGI PARK provides a rare rooftop pool and streamlined suites with leafy views over the treetops.

April: Scottsdale, Arizona

The ultimate way to end a relaxing day with friends is a terrace dinner at Four Seasons Resort Scottsdale at Troon North.

Sun-soaked days, temperatures in the high 70s and a relaxing atmosphere make Scottsdale an unmatched choice for a group recharge in April (and unlike some of the state’s more remote destinations, it’s just 15 minutes from Phoenix Sky Harbor International Airport, letting you start your vacation that much sooner). Peak season in the Sonoran Desert brings the ideal balance of mild mornings for scenic hikes, afternoons of poolside lounging, alfresco dining and evenings spent stargazing. Beyond the standout weather, Scottsdale is known for its sprawling resorts, championship golf courses and towering cacti. Your crew can check in to The Canyon Suites at The Phoenician, A Luxury Collection Resort, Scottsdale for mixology classes, massages and dips in the infinity pool, or prioritize self-care with facials, tennis and fire-warmed casitas at Four Seasons Resort Scottsdale at Troon North. But a trip to Scottsdale doesn’t have to be all about unwinding. For a change of scenery from resort life, downtown has many bars and restaurantsOpens overlay, such as ÉlephanteOpens overlay and Maple & AshOpens overlay.

May: Maui, Hawaii

An outrigger excursion that requires teamwork is as good a friend-bonding activity as any.

Maui is perfect for a group getaway, where everyone can embrace vacation mode while soaking up mood-boosting sunshine and reconnecting with nature. And while it’s on the longer end of domestic flights, it’s well worth a little more airtime to dip your toes in the turquoise tides. May is a particularly good time to visit for clear waters for snorkeling and a more mellow atmosphere, since you won’t have to deal with the spring break crowds or the summer vacation masses. For a fun and active group itinerary, start the day with oceanfront yoga, book a surf lesson or take a hula class. Then, rent an SUV so the whole crew can ride comfortably along the Hana Highway, a narrow, 64-mile-long ​road ​through lush vegetation, waterfalls​ and ​photogenic lookouts. After cruising around the island, head back to Four Seasons Resort Maui at Wailea for spa sessions, pool time and mai tai–making classes, or hop over to a neighboring property for a beachside luau.

June: Comporta, Portugal

Comporta’s secluded beaches are the ideal spot for a beach day—just you, the golden sand, the turquoise water and your pals.

Coworkers turned real-life friends can take advantage of quieter summer months with a relaxed escape to Comporta, an in-the-know coastal enclave less than a two-hour drive south of Lisbon. The small, walkable village is dotted with stylish shops—pick up a handmade friendship bracelet or linen twinsets to swan around in during your trip—and breezy eateries for seasonal sharing plates. Praia do Carvalhal is a popular sandy beach with palapa-shaded sun loungers you can rent out for the day and vibey but low-key restaurants right on the sand. For an unforgettable experience, book a sunset boat cruise around the Tróia Peninsula. Surrounded by umbrella pines and cork trees, Sublime Comporta has bunk-with-your-bestie rooms that come equipped with queen beds, suites with pools that open up into the lagoon and five-bedroom villas that provide ample space for your crew to spread out.

July: Oceanside, California

Oceanside has a clutch of great restaurants for group dinners; Valle, above, has Mexican wine pairings worth writing home about. (Deanna Sandoval/The Infatuation)

Located less than an hour’s drive north of San Diego and just 15 minutes from the many attractions in Carlsbad (because you’re never too old to pose for photos at The Flower Fields), Oceanside makes for a sun-splashed, fun-filled July escape. It’s great for low-maintenance groups who are happy with good weather, pretty Pacific vistas and tasty food. Primary draws include the sandy beaches and Oceanside Pier—at 1,954 feet, it’s one of the longest wooden piers on the West Coast. The on-the-rise SoCal city also has a great dining sceneOpens overlay, with lauded restaurants like ValleOpens overlay, which does chef’s tasting menus and Mexican wine pairings, and the more casual AllmineOpens overlay for artisanal pizzas. Travelers staying at Mission Pacific Beach Resort can expect ocean-view rooms, sunset cocktails on the lively rooftop and beach chair setup service.

August: Cotswolds, England

A walk through the Cotswolds with friends promises fond memories and frame-worthy photos.

While the rest of Europe (and the Americans who decamp across the pond for one last summer hurrah) are fighting over shorelines in southern Italy or the Balearics, you and your friends can wisely opt for a bucolic inland option that trades the scene for serenity. Located just 90 minutes from London, and accessible via train or car, the Cotswolds is a postcard-worthy stretch of the British countryside (one of Chase Travel’s 26 trips to take in 2026) with rolling farmlands, honey-colored stone towns and plenty of pastoral attractions, including historic castles and protected parklands. In August, it’s not too hot or humid, and the cooler spells of September have yet to set in, making it a splendid time for arboretum visits, strolling around the villages of Upper and Lower Slaughter and alfresco lunches. Pals can shack up in an eco-chic tree house at The Fish Hotel or go splitsies on a cottage rental in Oxfordshire.

September: Athens Riviera, Greece

Imagine sitting at a seaside restaurant on the Athens Riviera, toasting to your friendcation with a chilled bottle of Assyrtiko.

If that summer trip didn’t quite make it out of the group chat, pick a place that extends the warm-weather vibes into September. Of the many sun-drenched Greek destinations for sipping Assyrtiko, sharing fresh-caught grilled fish and ogling ancient ruins, the Athens Riviera (one of Chase Travel’s 26 trips to take in 2026) is particularly compelling for its proximity to the vibrant capital, just a 20-minute car ride north. The fall, with its thinned-out crowds and more forgiving (but still plenty warm) temperatures, is a lovely time to visit. Whether the group energy leans more toward a buzzy beach club or a private cabana at a luxury resort, you’ll have easy access to the sparkling Aegean Sea. And you’ll be close enough to the city to do a guided group tour of the Acropolis, browse the handmade ceramics and local jewelry boutiques (no, friendship bracelets aren’t just for tweens) and go out on the town before retiring to a stylish suite or multi-bedroom private residence at One&Only Aesthesis, a fashion-set favorite on the beach in Glyfada, for a good night’s sleep lulled by the sound of the waves.

October: Asheville, North Carolina

Cozy up by the fire at Grand Bohemian Lodge Asheville, Autograph Collection with your nearest and dearest.

With over 100 varieties of deciduous trees and seemingly endless mountain landscapes, Asheville is one of the best leaf-peeping destinations in the country. Visitors can view the fiery hues at the many local and state parks, The North Carolina Arboretum, Pisgah National Forest and the grounds of the historic Biltmore Estate. Of course, an October trip doesn’t have to be all about foliage chasing. Set amid the Blue Ridge Mountains, Asheville also welcomes creative crews, foodies and groups looking for a more offbeat escape. It has many breweries, live music venues, eclectic restaurants—with everything from nautical New American at The AdmiralOpens overlay to casual walk-up burger jointsOpens overlay—and the River Arts District, a community of artists’ studios, galleries and collectives that’s currently undergoing rebuilding efforts following the devastation of Hurricane Helene in September 2024. Grand Bohemian Lodge Asheville, Autograph Collection, a grand hotel built in the style of a 19th-century hunting lodge, is a solid choice for spacious accommodations and outdoor access. Crews who prefer to bunk all together will appreciate the spacious apartment-style setups at Elevation Lofts Hotel downtown.

November: Dubai, United Arab Emirates

Everything is bigger in Dubai—including the umbrella-lined swimming pools at the five-star resorts.

Few places match the glitz and glamour of Dubai. It’s the ultimate gold-dipped destination for an over-the-top getaway to match the energy of your most extra friend. Spend your time here bopping from glittering skyscrapers like the Burj Khalifa, the world’s tallest structure, to long-standing souks and mega malls brimming with high-end stores. The larger-than-life luxury resorts like Jumeirah Burj Al Arab have 24-karat-accented interiors; opulent spas replete with mosaic-clad saunas, herbal steam rooms and cold plunges; and sprawling heated swimming pools that range from relaxing to party-forward. For something sleeker and more subdued, check in to The Lana, part of the Dorchester Collection. The City of Gold is also awash in world-class restaurants where you can have decadent dinners that you’ll remember long after you’re back home eating takeout on the couch.

December: Rio de Janeiro, Brazil

The cable car ride up to Pão de Açúcar offers one of the city’s best vantage points.

For a warmed-up year-end getaway that leans deeper into local culture and nightlife than lounging at a resort, head to Rio de Janeiro. Brazil’s second-largest city has a little bit of everything: a rich history, stunning beaches, a lively atmosphere and December daytime temperatures that hover in the high 80s. Hot days are prime for soaking up the scene on the world-famous beaches of Ipanema and Copacabana—and when you’ve had your fill of sunshine, you can head over to the Museu de Arte do Rio, taking refuge indoors to admire the art, then finish off the day with a cable car ride up to Pão de Açúcar to catch some spectacular sunset views. Rio is defined by its energetic evenings, from traditional restaurants serving specialties like feijoada to cocktail bars and pulsing samba clubs. Fortunately, quiet, well-situated boutique hotels like Hotel Fasano Rio de Janeiro offer a stylish seaside retreat where your group can recover after big nights out.

Lead photo courtesy of Cap Juluca, A Belmond Hotel, Anguilla.