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Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.

At Pile Gate, the Old Town’s main entrance, descend the staircase to a landing near the small fountain (formerly only for Jews) to experience a moment of serenity, looking at this quiet bay bracketed by the mighty fortresses of Lovrijenac and Bokar. Kolorina means “calm harbor” and is the starting point for several kayak tours around the City Walls and the island of Lokrum. (The bay was also the location for the bloody Battle of Blackwater scene in season two of Game of Thrones. )

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

Moorings Village has a setting out of an island fantasy, stretched along one of the largest private beaches in the Keys, with more than 1,000 coconut palms shading its 18 guest villas. After a direct hit from Hurricane Irma, the resort reopened in January 2018 with 100 newly planted coconut trees, a new picturesque dock, and a refurbished swimming pool—while still maintaining its eclectic design and luxurious feel. The individually styled villas—each with a wraparound veranda—have kitchens, living and dining spaces, and a selection of artwork collected during resort owner Hubert Baudoin’s travels. Ocean activities rule the day here (unless you’re lolling in a hammock) and the property offers complimentary kayaks, paddleboards, and bikes, in addition to coordinating excursions like scuba diving, kitesurfing, sailing, and fishing. And because the resort takes up both sides of the Key of Islamorada, guests can catch the sunrise and then witness sunset while dining at either Pierre’s (an upscale spot with French fusion cuisine) or the Beach Café (a casual bistro serving Caribbean-American food). Pro tip: Book your visit to coincide with the full moon to attend the Mooring’s monthly beach party for live music, fireworks, and bonfires on the beach.

“I am grateful” is just one of the ways you order lunch at Cafe Gratitude. “I am whole” is another; as is “I am glorious.” Every dish on the menu has a name like this, and whether you’re in the mood for gratitude (the community bowl with shredded kale, black beans, garlic tahini, and quinoa), wholeness (the macrobiotic bowl with braised butternut squash, adzuki beans, and sautéed greens), or glory (the blackened tempeh Caesar wrap), Cafe Gratitude guarantees your meal will be as much an experience in self-affirmation as a delicious jaunt into vegan fair. The Venice location is eclectic in patronage and airy in design, while the swanky Larchmont restaurant draws a more Hollywood cast of characters. Other locations include the Arts District, Newport Beach, Beverly Hills, and a little further south in San Diego. For larger events, Cafe Gratitude can also be hired for catering services.

Wonderful catamarans that you can rent right off the beach.

Cane’s chef and owner Paul Yellin grew up on Barbados, and he drew on this experience while putting together this bar and restaurant: the menu is full of Caribbean dishes, and the space is decked out with palms, corrugated metal, and bamboo. Another Barbados-inspired touch? The heavy presence of rum at Cane. The bar houses bottles from across the wold, and the drinks menu serves classic rum-centric cocktails like Zombies and Painkillers alongside more creative concoctions.

This funky spot stands out among Amsterdam’s many urban “beach bars.” You can laze away a sunny afternoon at one of the picnic tables or chairs set up on a wide stretch of sand. Cocktails and beer slake your thirst, while decent pulled-pork tacos, burgers, and poke bowls keep hunger at bay. If the weather isn’t agreeable, the café—located inside a converted warehouse—strikes all the right hipster notes: Think distressed, graffitied concrete walls; leather sofas; vintage television sets; and groovy lighting. An adjacent warehouse hosts all sorts of events, from flea markets to film screenings to dance parties.

It’s a crime not to order a cocktail (boozy or virgin) at Spago’s terrace bar, situated next to the famous infinity pool on Marina Bay Sands’ breezy veranda. The drink menu is just as beautifully curated as the decor, featuring more than a dozen original cocktails, over 600 bottles of wine, and an extensive champagne list. Celebrity chef Wolfgang Puck put together the selection of bar bites, including Spago L.A. originals like the bigeye tuna tartare cones. For a full dinner menu in an even more refined setting, book a table in Spago’s glassed-in formal dining room to enjoy dishes like chirashi sushi from the legendary Tsukiji Market and pan-roasted snapper laksa.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Vancouver’s serene waters serve as the perfect playground for kayakers and stand-up paddleboarders. Newbies can book two-hour “tasters” at Ecomarine’s Granville Island or Jericho Beach locations, while more adventurous paddlers—of any level—can jump right into tours, like the summer sunset excursion along the scenic shores of False Creek (a protected inlet) and English Bay (part of the Strait of Georgia). While most tours last a half or whole day, Ecomarine also offers more hard-core expeditions, like the weeklong trip to Haida Gwaii. This craggy, rain-forested archipelago is often referred to as Canada’s Galápagos for its vast number of endemic species. It also has a wealth of First Nations heritage sites just waiting to be explored.

The edges of the iceberg (technically, bergy bits) are a great place for animal sightings. Harbor seals ride the floes, basking in the sun; orca whales prowl just around the ice barrier, waiting for an unwary seal to come out to where the whales’ sonar can reach. Humpbacks feed off krill upwellings, and bald eagles are as common as sparrows. Those who are very lucky (and who have good spotting scopes) can see mountain goats on occasion. They’re a wonder in the wild: How does a goat get up 3,200 meters of rock?

No island getaway is complete without seeing gorgeous scenery you’d never, ever see at home—and Willemstad’s floating bridge delivers! Built in 1888, “Our Swinging Old Lady” is supported by 16 pontoon boats and two motors. When you hear the siren, look to see the entrance gates slam shut and moments later, the bridge sways to accommodate passing ships. (If you don’t feel like waiting for Queen Emma to reopen, you can take a ferry between Willemstad’s Punda and Otrobanda districts instead.) At night, the bridge’s lights cast a shimmering rainbow on the water.

Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.

Built in the 1920s by a Croatian businessman, Palacio Astoreca underwent two years of refurbishment and restoration before opening its doors as a boutique hotel in 2012. The work was carried out to a meticulous degree, maintaining the original parquet floors, and adding splashes of color with art deco furniture and modern art, including one piece by Switzerland’s Frédéric Clot. The stucco-and-brick mansion rises up from the streets of Chile’s port city, Valparaíso, like a piece of red-and-white confectionary.

A statement staircase winds up to the 23 rooms, some of which have stand-alone bathtubs. And the basement level is home to a small spa with an open-air, wood-fueled hot tub set alongside a living wall. The reception level and entrance hall open out onto a terrace where lunch, tea, and cocktails are served, allowing guests prime views over the hilly city and Pacific Ocean. There are quiet corners for those seeking a solitary moment, including a library and a piano bar, which comes to life in the evenings with live music.