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Rebecca Walker embarks on a spontaneous journey to Bulgaria, guided by locals she connected with both virtually and in real life.

Antigua (pronounced An-tee’ga) encompasses 108 square miles of coastline and 365 white sand beaches between the Atlantic Ocean and the Caribbean Sea. For an uncommon, all-inclusive Caribbean holiday, stay at The Galley Bay Resort and Spa. In and around the property are ruins of forts hundreds of years old, wrecks for snorkeling, a spa with tree houses for treatment rooms, plenty of authentic dining options, and even world-class sailing opportunities.

From trinkets and tchotchkes to silver jewelry, high-quality hand blown glass, and the pottery of your dreams, the shops on the Baja Peninsula can cover your every spending whim. There are plenty of clothing shops too, if you forgot to pack enough bathing suits or some beach-to-dinner-perfect flip-flops. Between San José del Cabo and Cabo San Lucas, you can shop an art gallery or 12, open air markets, and shopping malls.

St. John is the least developed and most sparsely populated of the three main islands in the U.S. Virgin Islands. That’s not surprising, since more than half its land is protected as a U.S. National Park. Most visitors reach St. John by ferry from St. Thomas, landing at the dock in Cruz Bay, St. John’s main settlement. A village with only a few thousand residents, Cruz Bay has gained a reputation as an upscale retreat for movie stars and other high-profile people looking for a secluded getaway.

It all started back in 1956, when businessman and conservationist Laurance Rockefeller, who had bought extensive land holdings on St. John, opened the low-key but luxurious Caneel Bay Resort. It’s still going strong, and visitors can stop in for lunch and a swim in the beautiful bay. Rockefeller later donated much of his estate to the national park.

Snorkelers should make time for an underwater tour in Trunk Bay, where the National Park Service maintains a submarine snorkeling trail. And no sightseeing drive around the island is complete without a stop to see the fabulous panoramic view from the Bordeaux Mountain Overlook. Back in the town, the boutiques at Mongoose Junction offer one-of-a-kind souvenirs, while Cruz Bay Landing is a perfect spot to grab lunch and drinks.

Part of the Inn of the Governors, the rustic, casual, saloon-style vibes of Del Charro beckon one to relax and stay awhile. Try the signature house margarita (a mere $6.50), though the fancier, classic Silvercoin Margarita (a mix of Don Eduardo Silver Tequila and Cointreau) is mighty tasty, too. If you’re hungry, the green chili cheeseburger is a crowd-pleaser.

While hiking in Cape Town, there are plenty of moments when you’ll stop for a water break, wipe the sweat from your brow, and ignore those voices inside yourself saying you can’t possibly take another uphill step. This moment is fleeting, however, and always superseded by the lasting memories of when you feel like you’re on top of the world at the end of your hike. Silvermine Nature Reserve is 20 minutes from the city center and the part of Table Mountain National Park that covers the Cape Peninsula near Kalk Bay and Muizenberg. The Echo Valley hike can be approached from the Silvermine entrance on top of Ou Kaapse Weg (one way), or, from the entrance on Boyes Drive in Kalk Bay.

Spending two weeks in eastern Jamaica? Start in Port Antonio, head to Boston Bay and Long Bay, and end in the majestic Blue Mountains. Eastern Jamaica offers wide-ranging natural beauty in which to play: Two weeks is plenty of time to swim in secluded coves and walk deserted beaches, hike to jade pools and waterfalls, surf the waves of Boston Bay, explore ruins and forts, raft across the Rio Grande, bike at 7,000 feet, and, of course, sample both original Jamaica jerk and reggae.

It can be argued that just about any day in Miami is a perfect day – but choices must be made, right? Start the day South Beach, with a stroll along the beach or the Art Deco district before grabbing lunch; spend the afternoon shopping on Lincoln Road or take a relaxing cruise on Biscayne Bay. Head downtown to enjoy dinner with views over the city and bay, followed by some late-night music and fun back in South Beach.

The best hotels in Antigua are all about beach access and poolside lounging. Fulfill your private island fantasies at Jumby Bay, set on a private 300-acre island 10 minutes by boat from Antigua. Antigua’s Curtain Bluff Resort has one of the island’s most envious settings straddling two beaches, while guests at the St. James Club & Villas hotel have to choose between the beach or six different swimming pools. Foodies should be sure to book a reservation at the restaurant at Carlisle Bay.

AFAR chose a destination at random—by literally spinning a globe—and sent Sloane Crosley on a spontaneous journey to Ecuador.

While there are a growing number of beach resorts on St. Kitts, you can still find plenty of secluded sands around the island when you want to disappear for a few hours. Visitors can also look forward to sunbathing on the black sand of Dieppe Bay, spotting dolphins on Turtle Beach, or snorkeling over shipwrecks in White House Bay.

In the city’s once-gritty fishermen’s quarter, a group of activist chefs is reviving—and reinventing—traditional cuisine.

Jamaica is much more than just the beach. The island’s great outdoors includes thick rain forest, numerous waterfalls, rivers on which the sport of rafting was born, swimming holes, and more. Jamaica’s natural beauty has been the set for more than one Hollywood movie, and if you really can’t drag yourself away from the beach, the bioluminescent bays offer a different form of outdoor adventure.

Known for their ability to combine comfort with luxury, Dominica’s best accommodations range from oceanfront cabanas and cliffside condos to a hotel in a former military fortification and an eco-lodge on a working fruit plantation. Many focus on sustainability and adventure travel, while others highlight local art, world-class spas, and proximity to Dominica’s best beaches.

If you only have three days in Miami, you can still get a good feel for the Magic City. Explore South Beach’s Ocean Drive and the historic Art Deco district, head to the Design District for art museums and modern architecture, take a leisurely cruise on Biscayne Bay or an Everglades tour, and groove long into the night at one Miami Beach’s velvet-rope nightclubs.