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Definitely the coolest restaurant on the block, Model Milk, housed in a former dairy building, does eclectic fine dining in a rustic-hip setting (think exposed brick, and uncovered light bulbs dangling from salvaged wood). There’s nothing stuffy about Chef Justin Leboe’s menu of foie gras with smoked maple, and bacon-like steaks of Broek Acres pig with crushed edamame, apple, fennel, and celery. The best deal is the $35 prix fixe Sunday Supper, a full four-course meal served family style. While the menu varies, it doesn’t stray far from its soul food theme: romaine with chipotle and Stilton cheese, prawn ceviche, braised duck coleslaw, buttermilk fried chicken, plank-grilled mackerel, risotto-like jalapeño-cheddar grits, Mexican green beans, and hot and creamy potatoes. Besides the price tag, the best part is the blueberry shortcake for dessert.

Chef Franck Dangereux (formerly of La Colombe, a celebrated Cape Town institution) runs the Foodbarn Restaurant out of a lovely old barn in the village of Noordhoek. Here, you’ll get all the flavors of a fancy restaurant, without the fuss. You may dine on artistically presented dishes like pépé goat cheese beignets, but a glance around the revamped space, with its rustic-chic decor and colorful knickknacks, will remind you that you are, in fact, feasting in a barn. At night, the place transforms into a tapas bar.

Nestled between pristine beaches and lush forest, the peaceful town of Watamu is ground zero for water sports in Kenya. One of Kenya’s most renowned kite-surfing schools, Tribe Watersports, is based here and offers three–day courses to get you skimming the warm waves of the Indian Ocean in no time. If you’re happier underwater, Watamu will also appeal. A maze of rich coral reefs skirts the shoreline, so giant turtles and exotic fish can be seen year-round, and at certain times of the year majestic whale sharks pass through this region, making it a snorkeling and diving haven. For accommodation, check out the eccentric and charming Watamu Treehouse.

The newly refurbished Sheraton Kona Keauhou Bay Resort is stylish, with a large pool and water slide. But it was the history and the view from the hotel (located off the famous Ali’i Drive) that won me over. The hotel gives you an excellent vantage point to the bay around which King Kamehameha III was born (stillborn, as legend has it). He grew up to become Hawai’i’s powerful and benevolent ruler, and sought to unite the people. He called The Big Island his home and is beloved by many. The hotel offers several notable cultural markers, including two heiau (Hawaiian temple) replicas.

The museum’s collection and calendar of exhibits is a little more daring than you might imagine, but the permanent installation of James Turrell’s Knight Rise presents visitors with the biggest art jolt of all. The work, open to the public for free, consists of a circular bench beneath a luminous domed ceiling. An elliptical hole cut into the top of the dome contains a glimpse of sky. When observed in this manner, even the clearest desert sky seems to shift and pulse and fill the window with pure exuberant color. Come at dawn or sunset for the best (and often most solitary) viewing.

At 4,235 acres, Mission Bay Park is the largest man-made aquatic park in the U.S. Here, water-sports enthusiasts can enjoy everything from kayaking, windsurfing, and wakeboarding to snorkeling, scuba diving, and fishing, while landlubbers can take advantage of several trails and grassy areas. For equipment rentals, head to the Mission Bay Aquatic Center, located right on the bay.

A real Western experience is easy to come by at the Yellowstone Valley Lodge. The Lodge includes a number of beautiful cabins and a restaurant situated along the Yellowstone River in Montana‘s spectacular Paradise Valley. The lodge is known for the bespoke touches found throughout the property, from the food in the kitchen to the design of the cabins. This is one of the finest Yellowstone National Park bases you’ll ever find, and perhaps the only one you’ll ever return to after a night or two of falling asleep along the river.

Perhaps it’s more interested in diner loyalty than in snagging prizes, but chef Elena Reygadas’s original Mexico City restaurant is still beloved—and busier than ever. So while a few greatest hits linger season to season, there’s always something new to try, inspired by food of the Mediterranean (or the Middle East, or Paris) but supported by the just-picked ingredients only Mexico knows. It invites repeat visits where patrons count on impeccable breads and pastas, delicate greens, and sauces that never cloy or overwhelm, plus some of the freshest fish and tenderest viands to be had in the city. The setting—a venerable town-house patio and parlors, decorated in florid, provincial filigree and anchored by lovely vintage furnishings—is one of the city’s most romantic.

One of St. John’s most beautiful seaside spots, Hawksnest Beach offers a beautiful and easy-to-reach locale with convenient parking, picnic tables, barbecue grills, and ample shade. That accessibility, alas, can mean crowds, so try to arrive early and find your spot on the sand. A long snorkeling reef begins a few yards from the shore.

This enormous underground mall is where locals come to shop for electronics, clothing, shoes and accessories at bargain prices. This is a great place to pick up souvenirs, from chopsticks to inexpensive qipao (traditional Chinese dresses). Among the hundreds of shops are inexpensive restaurants serving dumplings, noodles and bubble tea (milk tea with tapioca pearls).

Not far from the white-sand beach within the Four Seasons Costa Rica, Bahia restaurant is the physical and spiritual heart of the resort, with a casual vibe by day and a cozy feel by night, thanks to soft mood lighting and a nightly live band. A wood-fired open kitchen serves a Latin American-inflected, regionally-sourced menu: Try the octopus carpaccio, or the grill menu’s enormous Pacific blue prawns with locally grown heirloom tomatoes and a side of sweet plantains.

New to the Isle of Harris, this is one of Scotland’s more promising distilleries to open in recent years. Here, five local men, trained from scratch in the art of distilling, are working hard to create a whisky of real provenance. You’ll have to wait a few more years to try The Hearach, but it’s made from the softest of Hebridean waters and aged in only the best bourbon barrels from carefully chosen Kentucky distillers, promising a dram with a signature Isle of Harris taste. In the meantime, visit the distillery to taste its popular gin (made with everything from traditional juniper berries to sea kelp) and tour its modern facilities, located right on the harbor in the town of Tarbert.

A recent addition to the Puerto Rican capital’s culinary scene are food hall–style spots where diners can choose among multiple kiosks, or stalls, each featuring a distinct kind of cuisine. Lote 23 is one such spot, located in the working-class neighborhood of Santurce. More than a dozen food entrepreneurs have fare on offer here, from pizza and tacos to bao and burgers. If you just need something to cool yourself off in the tropical heat, there are popsicles and cocktails, too. The alfresco eating area has plenty of picnic tables where you can sit and enjoy whatever you’ve ordered.

These days, a hip design hotel isn’t worth its salt unless it’s also home to an almost painfully trendy bar. But when Story Hotel first opened in 2009, on the border of two of Stockholm’s coolest neighborhoods, it set the standard to which all of the city’s subsequent boutique hotels would be held. The Story formula is deceptively simple: take one historic building in an achingly cool European capital and strip it down to exposed brick and concrete, and original hardwood floors, before decorating it with a sleek, unpretentious style that epitomizes Scandinavian design. Add a sprinkling of colorful graffiti art, and pair faded Persian rugs with collaged photographs and leather chairs. Make sure some rooms are small and affordable, while others are spacious and decadent.

The cuisine needn’t be fancy, but it ought to be high quality, just as the cocktails must be inventive and delicious. And don’t let the DJ-accompanied scene turn pretentious; everyone should feel welcome, and among friends. Story’s formula works, and there’s a reason this original boutique hotel is still one of Stockholm’s best.

Make the Gibraltar shopping circuit: Admire unique wares made by local craftspeople at Gibraltar Arts and Crafts in Casemates Square. On Main Street, stop and smell the handmade soap and beauty products at Gibraltar Soap. Then browse the quirky paper goods and kitsch crafts at All Wrapped Up or find the perfect accessory at the Silver Shop.