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Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.

Chef Laurent Tourondel’s LT Steak & Seafood, located inside the historic Betsy Hotel on Ocean Drive, is popular not just with hotel guests but locals as well, who stop in for an afterwork cocktail or a nice night out. The restaurant does what its name indicates, and the menu is evenly divided between prime cuts of porterhouse and rib eye and fresh seafood from local waters and elsewhere, as well as sushi, sashimi, and ceviche. At dinner, there is often live entertainment such as jazz in the conservatory or a performance by an opera singer.

The most stylish spot in Fort Myers’ River District, Firestone occupies a historic, four-story building right on the water. In the restaurant, guests enjoy steak and seafood specialties paired with fresh, local produce. Also onsite is the rooftop Skybar, open daily from 4 p.m. for sweeping views of the Caloosahatchee River and Downtown River Basin, as well as a special martini bar, which welcomes patrons on Friday and Saturday nights.

Located in the middle of New York harbor, less than half a mile from Manhattan (and even closer to Brooklyn), 172-acre Governors Island feels like a world unto itself, far from the bustling city. It has played a key role in the defense of New York at various points and two fortifications here, Fort Jay and Castle Williams, reflect that history. From 1966 to 1996, the island was a Coast Guard station; since it closed, the city, state, and federal governments have discussed various plans for the island’s development. In the meantime, it is open to the public for six months each year, from May 1 to October 31, when it is possible to wander among the Coast Guard barracks, visit the commander’s house, and bike around the mostly car-free island. Ferries depart from both Manhattan and Brooklyn starting at 10 a.m. and running until 6:15 p.m. on weekdays and 7 p.m. on Saturday and Sunday. During many weekends in the summer, art fairs, food festivals, and other events help draw visitors to the island, but even if you go on a day without anything special scheduled, a journey here provides a refreshingly different perspective on New York.

An archipelago within an archipelago is already an astonishing fact to grasp, but Îles des Saintes, made up of nine islets, only two of them inhabited, is full of yet more surprises. Hop on a daily ferry ride south from Trois-Rivieres in Basse-Terre to these gorgeous offshore islands around a stunning aquamarine bay dotted with sailboats and hugged by coral reefs. Also known as Les Saintes, these islands combine a traditional Caribbean setting of secluded beaches, forts, and towering palm trees with a chic French village lifestyle. The streets here are free of cars, the winding roads to be explored by electric scooter or on foot. Hike to Fort Napoleon for a breathtaking panoramic view over Les Saintes Bay, explore the surrounding waters by catamaran, go diving off the bluffs, sample some of Guadeloupe’s best French and Creole fusion restaurants, and shop the boutiques for French fashions and local jewelry.

One of Bermuda’s most historic resorts—there’s even a 300-year-old sea captain’s cottage on the property—Cambridge Beaches is a traditional rose-hued confection that matches its four pink-sand shores. Though an English country club vibe prevails in many of the public spaces (think tennis whites and croquet on the lawn), the rooms are anything but stuffy, outfitted with vibrant coral and lime-green sofas, zebra-striped rugs, and in some rooms, private plunge pools. Relaxation can be found in the marine-sourced treatments on offer at the Ocean Spa, but if you’re looking to excite the palate, the acclaimed Tamarisk restaurant plates up local takes on creole specialties, from the iconic Bermudan fish chowder to fresh-caught lobster baked in garlic and coconut oil.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

The Maiden’s Tower, which seemingly floats in the Bosphorus off Asia, is one of the more popular symbols of the city. Once a Byzantine tollbooth and later an Ottoman lighthouse, it’s most famous for a legend involving a princess and a prophecy that she would die from a snakebite. Her father exiled her to the tower in the hope of protecting her but, alas, the prophecy could not be avoided—a snake made its way to the island, either in a bouquet of flowers or a basket of grapes (depending on the version of the tale).

Bogotá’s museum of all things gold is one of Colombia’s greatest treasures. Yet despite the name, you’ll find more here than just the precious metal. In addition to stunning displays drawing on a collection of more than 30,000 gold treasures, you’ll find highlights from the institution’s more than 20,000 artifacts of clay, textiles, and other materials that reveal the history of Colombia’s diverse pre-Hispanic cultures. Audio guides enhance the experience with information on the objects’ purpose and provenance that connects various periods and movements. The museum shop offers dazzling (if somewhat expensive) souvenirs fashioned by members of Colombia’s many indigenous nations.

In 1911, American star jockey Tod Sloan took a bar in Manhattan, dismantled it, and shipped it to Paris. At the time, American tourists and members of the artistic and literary communities were beginning to visit the City of Light in ever-increasing numbers, and Sloan wanted to capitalize on his fame and make the place a spot where expats would feel at home. Over the years, Harry’s New York Bar has been frequented by a number of famous Americans and international celebrities, including Sinclair Lewis, Ernest Hemingway, Coco Chanel, Jack Dempsey, Rita Hayworth, Humphrey Bogart and the Duke of Windsor. Whether or not you have star status, you can still settle in on a stool with a drink and soak in the history.

The Common becomes extraordinary on winter evenings when the Christmas tree is up and soft lights seem to hold back the twilight chill, but the truth is there’s no bad time to visit the nation’s oldest public park. The former cow pasture has been a focal point for Boston’s history and culture since its inception in 1636—a site for riots and rallies from the Revolutionary War to the Vietnam War era as well as weddings, hangings, and burials. Summer splashing and winter skating at the Frog Pond are local traditions, and you can spend hours wandering from landmark to landmark (like Augustus Saint-Gaudens’s famous bas-relief Memorial to Robert Gould Shaw and the Massachusetts Fifty-Fourth Regiment, or the Soldiers and Sailors monument atop Flag Staff Hill). Or you can just laze in the sun on the park’s west-side lawn.

Stretched out from the northwest corner of the island like a small arm, Pigeon Island is a historical landmark and a satisfying all-in-one nature, beach, and hiking escape minutes from Rodney Bay Marina. The 44-acre mountainous green plot is home to the preserved ruins of British military forts and garrisons; the Brits chased the Caribs out and used the islet to monitor French activity. Walk among the ruins, and hike up to the cannons of Fort Rodney, where the lookout point offers a breathtaking panoramic view of St. Lucia’s coastline and the sea below, dotted with sailboats. Hike down to the beach for a swim and a toast to history at Jambe de Bois, a restaurant on the water.

Rafting on the Martha Brae River—a float down a three-mile segment of the river on a 30-foot bamboo raft—provides a pleasant hour or so in one of Jamaica’s gorgeous ecosystems. Passengers can slip into the water and swim beside the raft, or look for birds in the lush trees along the river’s banks, or just sit back and be carried along. The staging area is 20 miles away from Montego Bay.

Leave it to Disney to give visitors the chance to travel the world without leaving a theme park. At Epcot’s World Showcase, you’ll find several countries re-created to surprisingly realistic effect, all surrounding a centerpiece lagoon. Experience the landscapes, food, and cultural performances of such diverse lands as China, Italy, Canada, and Morocco, or embark on a “drink around the world” journey by grabbing a Hefeweizen in Germany, a vin rouge in France, a margarita in Mexico, and so on. The staff working in each area are natives of the country, so you can expect an authentic experience wherever you stop. Also worth visiting in Epcot are the 3-D rides, the Frozen-themed attractions, and the underwater coral reef. In addition, the park hosts annual events like the Epcot International Food & Wine Festival in the late fall, and the Epcot International Flower & Garden Festival each spring, making it more than worth a visit.

If swimming with dolphins is on your vacation bucket list, you’ll want to visit Dolphin Discovery. The center offers a variety of animal encounters in an enclosure near the Bird Rock Beach Hotel on St. Kitts’ south coast, just outside Basseterre. Depending on which program you choose, you can expect dolphin “kisses,” fin rides, and a “foot push,” during which a pair of dolphins will lift you out of the water.