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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.

Montego Bay and the west coast of Jamaica attract first-timers to the island, and it’s easy to see why: white-sand beaches, the most glorious sunsets in Jamaica, plush resorts, a wide variety of restaurants, and a lively music scene. But there’s also plenty to see and do in the west coast interior away from Montego Bay: rivers, cenotes, and waterfalls such as the stunning Mayfield Falls.

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.

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.

With settlement dating back to 1699, the “Little City” is named for The Falls Church, an 18th-century Anglican parish (for whom President George Washington was a vestryman). At only 2.2 square miles, this historic suburb of Washington, D.C. is known for its urban village community, nationally ranked school system, restaurants, and a thriving Hispanic and Vietnamese community.

Regularly ranked as the most literate city in the US, DC houses attractive independent and used bookstores for the bibliophile. Let’s not forget to mention that DC is home to the Library of Congress, the world’s largest library, which comprises of three buildings containing over 158 million items (36 million of them books in 460 languages) and the Folger Library, the world’s largest Shakespearean library. Definitely plenty of shelves and stacks for the literary nerd to get lost in.

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.

For cross-country skiers, one winter destination rises above the rest: humble Hayward, Wisconsin, where, for a glorious weekend, their obscure sport is king.

Home to over 150 active registered food trucks, DC’s food truck phenomenon is alive and well. From ethnic to comfort food, most trucks are situated along public squares, namely Franklin and Farragut Squares, and outside Metro subway stops such as Union Station, Metro Center, L’Enfant Plaza, and Rosslyn. With numerous options, locals and visitors can utilize the Food Truck Fiesta mobile app or website to track their favorite curbside eats in real-time by map and list format.

The give and take of a 20-year friendship.

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.

If eating huge plates of pork, deciphering local slang, and snowshoeing through the woods of Québec can’t bring two siblings together, what can?