It’s All Fun and Games at These 10 Hotels

This Art Deco landmark turned hip hangout in downtown Portland has brought back its popular "19th Hole" pop-up experience for summer. On SW 15th and Yamhill, just across the street from the hotel, you’ll find a breezy outdoor patio with a nine-hole miniature golf course, custom-made picnic tables, jaunty foliage, and umbrellas. Added bonus: the menu includes over 50 craft beers, Oregon wines, and Pacific Northwest ciders along with course-side snacks courtesy of Neesay (the food cart from local chef Jun Robles), which dishes up flavors from Korea, Japan, and the Philippines—perfect for noshing between rounds.

While this tony, family-friendly resort offers plenty of activities to help guests work up a sweat—biking along the 26-mile Cape Cod Bike & Rail Trail, tennis in one of the property's two top-notch tennis complexes, teeing off on Cape Cod's only Nicklaus Design golf course—we're more partial to the gentler sport of croquet, which can be played on the lush front lawn of the Mansion, a historic 1912 Victorian gem that's sure to make a splendid backdrop on your Instagram feed.

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Along with old-fashioned fun in the form of a volleyball court and cornhole right on the sand, this classic, 90-year-old Montauk legend on a stretch of gorgeous beachfront also offers a program of high-energy workouts in conjunction with health firm Wellthily. Guests can sign up for classes that include moves from cult New York fitness players like AKT, The Dailey Method, Cyc, Bari Studio, Y7, and Dance Body. The best part? Sessions are often held alfresco on one of the revamped hot spot's ocean-facing decks.

With its inimitable location in San Marco, on the tip of Giudecca Island facing the lagoon and Doge’s Palace, Hotel Cipriani has Venetian style down. When you've finished swanning around the grounds pretending to be in a Fellini movie, hop on one of the hotel's water bicycles and take a ride through the city of canals. The bikes are man-powered, so you'll get a workout while still living the dream of journeying along the Grand Canal, gliding past crooning gondoliers, under the Bridge of Sighs, and through the arch of the Rialto Bridge.

America's most outdoorsy state doesn't skimp when it comes to outdoor adventures, from skiing and mountain climbing to rafting to fly fishing. But if you're looking for some adorable company while working out your Fitbit, this swanky resort has just the thing: during one of their "Private Nature Experiences," guests can borrow one of the property’s resident canines, Bachelor (a Saint Bernard) or Belle (a Bernese Mountain Dog), to accompany them on a hiking adventure—picnic lunch and wine included.

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This legendary 1920s inn exudes quintessential New England style, from its gray shingled exterior to the lush green lawns rolling down to Nantucket Harbor. Guests gather on the lawn for competitive rounds of cornhole (for the uninitiated, a distinctly leisurely game in which players attempt to punt small bean bags into a hole in a raised wooden board), all while sipping cocktails and gazing out at the marine traffic in the harbor.

At this chic celebrity-magnet Caribbean hideaway, intrepid (read: ambitious) guests can get a group together and create their own island adventure. The "mini-triathlon" is comprised of a 2.5-mile kayak trip, a one-mile run through a working banana plantation, and a bike ride around the island—think of it as a heart-pumping fast track to experiencing the best of this tropical paradise. Wildlife lovers will particular enjoy the kayaking waterway, which has been hand-cleared so as to not disturb the ecosystems and is home to leatherback sea turtles and nurse sharks.

During "Surfing with the Chef," which debuts this summer at this Southern California coastal gem, Executive Chef Pierre Albaladejo takes guests from the stove to the sand in order to share his two passions—cooking and surfing. The day begins with an intimate breakfast in the kitchen, followed by surf lessons at one of the local Carlsbad beaches before concluding with a “toes in the sand” meal on the beach cooked by Chef Pierre himself. After lunch, guests will be presented with their own personalized longboard surfboard that can be shipped back home following their visit.

You’ll find ultra-chic lodgings with a laid-back Bahamian sensibility at this 96-acre private island resort, plus a slate of activities that include moonlit spear-fishing at midnight. After lobster season—a celebratory time around the islands—officially starts on August 1, guests can embark on an after-dark adventure to one of the top-notch diving sites close to the resort, where, with the aid of a snorkel and a spear, they can catch dinner for the following evening.

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This elegant Kyoto stay offers a buffet of incredible Japanese cultural experiences, including a sushi masterclass, playing dress-up with kimonos, origami making, and instructions on how to build your own Zen garden—but our favorite is the Samurai Experience. During this 75-minute class, guests learn all about the performing art of kenbu (literally “sword dance”), which ancient Japanese warriors used to prepare themselves for battle in feudal times. You'll learn basic kenbu moves with a real samurai sword while dressed in traditional costume, and, at the end, be treated to an unforgettable performance staged by a kenbu master.