The 10 Best Group Vacation Destinations

The only thing better than a vacation is a group vacation, because the only thing better than a break from your life is taking that break with your friends. That said, when you roll deep, it’s hard to nail down a destination with enough bars, restaurants, "everybody in!" photo ops, and activities to keep even the most ADD of your crew happy, day and night, without the big city sprawl. Fortunately for you, we did all the hard work, and picked the 10 ripest, mid-sized American spots for you and your crew to descend upon. 
 

Where to stay:The Hotel Telluride is famous for its rustic charm and sweet hospitality (we know it’s a hotel, but everyone say’s they’re like, real nice, OK?). Plus, it’s reasonably priced, less busy in the summer, and just a couple blocks from downtown, which saves multiple cabs. 
Carpe Diem: Telluride is the perfect spot to see what’s up with SUP-boarding .The views on the Alta Lakes, or the Down Valley Park, are downright delightful, and gliding along the glassy water, upright and by paddle, is the way to savor the surrounding cliffs slowly, like some beer-sipping basilisks (the lizards that can run on water). Or, if you want mo’ ruckus, rent ATVs from Telluride Outfitters, by the half or full day, and tear up all that scenic earth on four wheels. 
Carpe Noctem: Eat at Black Iron Kitchen & Bar, a mountainside eatery that’s big enough to accommodate your crew. At least one of you should try their specialty: steamed king salmon, quinoa, tempe, arame corn salad, and arugula frisée salad. Or head to Jerry Greene’s joint, Baked in Telluride (open since 1975), for pizza, plus local wine and beer. After, Main Street is packed with taverns, like the Last Dollar Saloon, fit for a well-lathered crawl.
Bonus group activity: Try not to break your neck/meet cool locals -- you can never have too many friends -- at the Telluride Town Park Skate Park.

Where to stay: This 8,000sq ft stone house has plenty of space to crash with six bedrooms, walnut floors, and a big-ass swimming pool. Rent it with your friends for $305/night.
Carpe Diem: Go on a private safari at the Lazy 5 Ranch, where you can cruise along and view exotic animals of all stripes (giraffes, ostriches, rhinos, etc.), and some animals of literally all stripes (zebras). Or, if a languid expedition in your own car is too chill for some of your crew, have them rev their engines at Victory Lane Karting. This spot is unlike whatever lame go-kart you’ve already tried -- it’s “European style,” and that (apparently) means its whips use Honda GX 270 RH 9HP, non-governed engines, which average 45 mph, so get ready to strap on a helmet.
Carpe Noctem: A trip to Charlotte is a total waste if your gang doesn't eat themselves silly touring the city's dynamic food scene. If you need a starting point, definitely make plans to eat Carolina-style BBQ at Midwood Smokehouse; their brisket is so good, and not remotely lean (which is why it’s very good). Check out TILT if you’re feeling flossy and want some dirty dancing in a chandelier-dangling club -- just look fresh, as there’s a strict dress code. If your posse’s not keen on the clerb, sip martinis at 300 East, or hit the Moosehead Grill, a bar that inhabits an iconic American red-roofed building (it was formerly a Pizza Hut).
Bonus group activity: Head over to the 500-acre US National Whitewater Center, the largest manmade whitewater river in the world. Other activities there: zip-lining, kayaking, and rock climbing.

Where to stay: This music-themed vacation home accommodates six for $290/night.
Carpe Diem: No food lends itself to sharing quite like BBQ (wait you were going to eat that rack yourself?) so make any stay in Austin meat-themed. To work up an appetite, cruise to New Braunfels and go tubing down the Guadalupe. Exit at Gruene to hang out at Texas' oldest country music dance hall (because you wanted to last time, but tubing and/or dancing by yourself isn’t cool, unless you’re Billy Idol). Then, rent a party barge on Lake Austin, which is basically right in the middle of the city. Def climb Enchanted Rock, the world's largest granite structure; it’s actually totally badass. 
Carpe Noctem: More BBQ, duh. And, no matter what sort of nightlife your friends are into, you'll find it -- from the well, dirty, at the Dirty 6th, where the streets are lit by live music, near everywhere, to more mature cocktailing at Rainey Street.
Bonus group activity:McKinney Falls kayaking/war-canoeing. 

Where to stay:Hotel Roanoke is a massive Tudor-style building (circa 1882); it’s restored so nice that it's listed on the National Register of Historic Places, so tell that crazy friend to keep his shoes off the furniture. Rooms start at $99/night.
Carpe Diem: Eat a proper Southern meal at The Roanoker, a local icon since 1941, and beloved for its biscuits (from-scratch biscuit-making is hard to get right and easy to ruin). Hike up to the top of Mill Mountain, 1,040 feet above Roanoke, a vantage point that unfurls miles of the craggily gorgeous Blue Ridge Mountains. At the summit, take a group photo at the Roanoke Star, the largest man-made light-up star anywhere (whee!), which has adorned the top of the town since 1949. 
Carpe Noctem: Check out some legit live gospel, roots and bluegrass along the famous Crooked Road, on Virginia's Heritage Music Trail. Since you’re deep in tobacco territory, you may as well stop in and enjoy the neon-lit Underground Hookah Lounge, which is both literally and figuratively “underground.” 
Bonus group activity: Check out the Community Arboretum, two acres of lush gardens with 700 distinct plant species. Or: catch a trucker outta Philly à la Bob Dylan.

With the right people, any spot can feel like a vacation spot.  Gather up your buddies and make it a mini-vacation any time, anywhere with Wild Turkey American Honey.

Where to stay: You and five friends can post up in this 190-year-old adobe for $385/night.
Carpe Diem:The Puye Cliff Dwellings have been a rockin’ spot since 900 AD, when Pueblo Native Americans first built their living spaces into the mountainside here -- think of it how your realtor would describe it: earthy, and pre-war. There are more than 700 rooms, enough to accommodate everyone you've ever met. Later, bug out at the Harrell House of Natural Oddities, where you can handle tarantulas, scorpions, and other desert-dwelling creepy-crawlies for a couple bucks, and determine which of your friends are yellow-bellied. Then, take a hike up Atalaya Mountain, which has several trails divided by difficulty, all of which provide a good view of the entire valley, no matter what shape your buddies are in at vay-cay time.
Carpe Noctem: Get seasonal cocktails at Secreto Lounge then head to The Den, in the downstairs section of the Coyote Café (where you should have gone earlier to eat innovative Southwestern cuisine). It gets weird in a good way around 1am, and local hero DJs spin right round.
Bonus group activity: Check out Madrid, a classic Old West mining settlement that went full ghost (town). After WWII, the eerily deserted spot is now a popular stop-off for both hippies and Hell’s Angels. It’s not exactly dangerous, but having your crew as backup isn’t exactly a bad idea, either.

Where to stay: Rent this “spacious oasis” downtown for $250/night; it’s an Old South four-bedroom house with chic furnishing. You guys have finally made it. 
Carpe Diem: In addition to historic sites like Fort Sumter, there’s the South Carolina Aquarium, and it’s dope as what, which is to say it’s packed with marine critters to scope out -- none of which have the complex limbic system and accordant emotional lives as orca whales, so relax you, there’s just fish and some turtles and other not-that-sentient sea stuff. Theatre 99 also holds improv and local theatre that beats a blockbuster any day. 
Carpe Noctem: The Charleston food scene is on fire right now, so arrive hungry. Check out The Ordinary for its excellent seafood and giant balcony, or the Craftsman Kitchen & Tap House's tavern-like vibe (brawls optional). Hit The Grocery for some low country fare, and be sure to catch Edmund's Oast -- possibly the beer bar in the South, and suitably enormous. 
Bonus group activity: Charleston has a lot of history, which naturally lends itself to good ghost tours, but then, so does the accent. One in particular, Bull Dog Tours, claims to offer all sorts, two of which are pub crawls and ghost tours, respectively. We called to see if you can combine them, and Janet says you can. 

Where to stay: This three-bedroom house, in the heart of Old San Juan, is cozy AF and accommodates 8 for $120/night.
Carpe Diem: Go to Condado Beach, and do whatever it is you do at a beautiful Caribbean beach. Then, walk around in Old San Juan, and be transported straight to a Spanish Colonial city, where pastel shades of green, pink, and purple flank cobblestone streets. Savor those tropical time-capsule sights, but don’t get so heady that you forget to go to Don Collins Cigars on Cristo Street, which has been around for five centuries, and where the first cigar is always free. If you don't take a group pic here, you are bad at vacations. 
Carpe Noctem: Before you suckle on a stoge like a Batman villain, sharpen up with $1 shots at Los 3 Cuernos. The au courant San Juan cocktail is called chichaíto, a traditional Puerto Rican after-dinner drink that’s been revived by the mod San Juan scene, and which you should learn how to say so you can order it (chee-chah-ee-tow, bro). Also, non-MLB baseball games here are really good and cost like two clams (USD).
Bonus group activity: Go to the Bacardi factory, learn why the bat is their logo, bring back small talk that’s relevant in any bar as a free souvenir for the friends you didn’t invite.

Where to stay: Stay at this spiritual space adjacent to the Coconino National Forest and the Sedona Sacred Rocks for $155/night; it accommodates up to 7 people.
Carpe Diem: Should you and your boys enjoy a more chill vibe, were Sedona not a town, but rather a girl you met at a party, she’d say she wasn’t religious, but she’s spiritual. By that we mean that there are four things locally called vortexes, described as energy vacuums (just relax and lean into it, man). Should visiting spas and pondering larger questions get a little too chill, try tubing at Slide Rock State Park: there’s a creek that runs over a bare bed of red rock, which is evidently slick and gives the place its moniker. There's also off-roading and abundant hiking and camping tours. 
Carpe Noctem:Full Moon Saloon has a very generous karaoke song selection, but Relics is really the spot to check out. It’s the oldest continually operating restaurant in town, where you should split the Tilapia and Prawn Napoleon. Depending on the night, there’s a jazz band, or a dance floor, or some other evening reason to come through.
Bonus group activity: Go to Red Rock State Park, enjoy its dramatic cliffs and rich color scheme, and then try to drop an anvil on a roadrunner.

Where to stay: This two-bedroom house on the Santa Barbara Riviera has views of the ocean and downtown, and a hot tub, for $240/night.
Carpe Diem: Hop aboard a boat bound for the Santa Barbara Channel, and check out the Channel Islands National Park, a string of five uninhabited islands, and enjoy abundant Californian flora and fauna, including dolphins, whales, seals, and sea lions. Or, if Mike had too many shots last night, hike up to the Gaviota Hot Springs; the trail is about 6 miles long, and there are two natural springs to soak in at its end.
Carpe Noctem: Eat at Sandbar, a Mexican restaurant with generous outdoor space, fire pits, and good eats. Then get down at the Blind Tiger, a three-story nightclub, equipped with throbbing bass, beautiful locals, and burlesque shows. Or check out Velvet Jones if you’re more into a dive-y space with live music. Old Kings Road is a great pub, and has the Spanish-style architecture, a hallmark of Santa Barbara that compliments the mild Mediterranean climate here perfectly.
Bonus group activity:Rincon Point is a famous point break, so rent a long board and hang ten, or just hang around an enjoy the surf show.

Where to stay: Rent this jewel box of a cottage downtown for $111/night.
Carpe Diem: A picturesque, unspoiled Floridian town is a rare thing, but Stuart proves that places under the mythic banner of “Old Florida” still exist. Its downtown is quaint, un-crowded, and consists mostly of locally owned businesses. To get a sense of it, take the Riverwalk, and people- or boat-watch, or hit up the Florida Oceanographic Coastal Center to get schooled on (and see) local marine life.
Carpe Noctem: Eat the pulled pork at Bono's BBQ & Grill for some smoky seaside fare. Check out Crush Bar on the weekend for a chill club with old school beats, or shoot pool at Stix Billiards Club. Terra Fermata Tiki Bar is a joint with tropical vibes, live & beach-y music, hammocks, tattered couches, and a giant Jenga game.
Bonus group activity: ​Since you’ve got a group, you can hire a private charter boat for deep-sea fishing, and catch your dinner. Dolphin fish, or as you see it on menus, “Mahi-mahi,” are all up in these waters. Pro tip: if you catch a “schoolie,” or a dolphin fish that small enough to cruise in a school, and not some big lone bull, leave the line in after you hook one, and the rest of the school will stay with it -- until you and your friends catch them. Just don’t devour the whole group, it's unsportsmanlike.