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AFAR chose a destination at random and sent writer Brett Martin with 24-hours’ notice to the most challenging island in the Caribbean.

A former Manhattanite returns to New York and rediscovers the city’s old charm through his child’s eyes.

A bluegrass fiddler travels to Vienna to learn how to sing—and how to embrace the city’s most famous art: opera.

Cairo Beyond the Headlines

Find comfort in taking a trip to help conserve the wildlife.

Tea house owner, Gaynor Salisbury, shares her favorite spots in Edinburgh.

AFAR chose a destination at random—by literally spinning a globe—and sent comedian Jorma Taccone on a spontaneous journey to Nairobi, Kenya.

Part third-wave coffee shop, part gallery, Distrikt is a great spot to enjoy high quality coffee as well as discover local up-and-coming artists. The exposed brick walls are perfect backgrounds for the rotating displays of artwork, as well as the café’s regular events, which include stand-up comedy evenings and even small operas. As well as locally-roasted coffee blends, you can also find whole-leaf teas and a brunch menu with antipodean influences.

When you live in Miami, you crave more than the glittery neon of South Beach. In Wynwood, the areas most up-and-coming hub for art and nightlife, Gramps appears like a grungy truck stop on the orange dive exterior. Inside, the bar includes live music, stand-up comedy and games. The bar serves creative speciality cocktails with flavorful, fresh ingredients. Outside, there’s an expansive patio with graffiti, art, picnic tables and live sports broadcasts projected on the buildings exterior. The vibe here is totally relaxed and vibrant. The crowd consists of hipsters, artists and fashionable hippies.

The modern minimalism of Le Méridien Chambers boutique hotel is accented by all things art. Graffiti-covered stairwells and hallways lead to rooms, each with their own original piece of art by the likes of Brits Damien Hirst and Gary Hume. Located in the vibrant Theatre District, entertainment from live music to stand-up comedy is just outside the door. As a guest, you’ll be granted free admission to the popular Walker Art Museum one mile away. Aside from the art, there are thoughtful amenities like the rain shower and heated floors, and fresh Italian cuisine at the hotel’s Marin Restaurant & Bar.

Part restaurant and part performance venue, the Rendezvous is a full night out in one cozy spot. The restaurant has typical bar food (burgers, salads, deep-fried snacks) that’s basic but good; happy hour goes from 3-6 pm daily with food specials. The tiny Jewelbox Theatre is an intimate cabaret-style theatre, where you’ll find everything from burlesque to comedy variety shows to live music and theater. They also have two excellent private rental rooms for parties. Upstairs, the Red Velvet Lounge looks out onto the main dining floor and has its own sound system. Downstairs, the basement-level Grotto is a dark, red-lit cave with its own private bar and plenty of room for dancing.

This independent bookstore feels like a cozy home, with rooms full of books and comfortable chairs in which to sit and browse. Fans of Dan Brown’s Da Vinci Code may recognize the shop as the one where Robert Langdon searched for Dante’s Divine Comedy. There is an extensive selection of English-language titles about Florence, Tuscany, and Italy that range from tiny novelty volumes to large coffee-table tomes. Head to the back and you will find a few shelves of secondhand paperbacks that provide material to read that doesn’t require Wi-Fi.

Almost unchanged since 1912, the Théâtre Corona (Corona Theatre) in Little Burgundy was built to host showings of silent films accompanied by live music and comedy shows by local troupes. You can still find an orchestra pit and the original dressing rooms under the stage, but since the late 1990s—after coming close to demolition—it has served mainly to host live music, by acts like Buck65, La Roux, and Arcade Fire. The heritage décor, with painted ceiling, gilded columns and heavy jacquard brocade curtains, and the relatively small capacity for 700 spectators, make this a singularly intimate place to see a show. The best sightlines are from the balcony, but there’s nothing like the feel of a smooth wooden dance floor beneath your soles.

The Glenn Miller Orchestra introduced America to the Chattanooga Choo Choo and Track 29 in the 1940s, but the train and its home at Terminal Station date all the way back to 1909. In 1973, the original Pullman train cars were converted into luxury hotel rooms, transporting guests to a past era of travel—albeit with modern amenities like high-speed internet, refrigerators, and coffeemakers. Spend the night at the hotel, or simply explore the former terminal complex, which now features multiple restaurants, bars, retail outlets, a comedy club, and a beautiful rose garden. At Gate 11 Distillery, you can even sample artisanal spirits straight up or in carefully crafted cocktails.

Standing in the Piazza Santa Croce, a statue of Dante looms over the square from the corner. Florence, where Durante degli Alighieri’s journey through hell, purgatory, and paradise was to begin but not end. In 1829 a tomb was built for him in the Basilica of Santa Croce—the largest Franciscan church in the world. The tomb has remained empty ever since as Dante’s body lies in Ravenna.