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

Charlotte Amalie is the capital of St. Thomas, and Frenchtown is a settlement just to the west of the capital. The name St. Thomas is rooted in the Dutch word Taphus, meaning “beer halls”—stemming from this once notorious port’s reputation as a lair for pirates and scoundrels. The name still fits these days, albeit not so scandalously, in Charlotte Amalie.

Celebrated worldwide for its culinary chops, Vancouver tops the list of British Columbia’s best stops for food-loving travelers. The city blends the freshest ingredients (oh, the sushi) with daring, modern techniques. Favorite dining stops include Blue Water Cafe, Cafe Medina, Kissa Tanto, and Vikram Vij’s well-named Vij’s. But those restaurants are just the start. A leader of the sustainable seafood movement in the Pacific Northwest and beyond, the city plays with a big palette, looking west to Asia for flavor inspiration.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

Philadelphia is known for its markets, but you can also find books, music, art, antique treasures, Pennsylvania handicrafts, and Whirly Berley Bars in the City of Brotherly Love. Whether you’re looking for high-end boutiques or vintage funk, Philly’s got you covered.

There’s a reason Blue Cave Castle (affectionately dubbed “BCC” by return visitors) has a following. Designed in the shape of a castle, it’s impossible to miss this dominating blue structure on Negril’s cliff side. Tower rooms offer dramatic views 50 feet above the sea, and yet surprisingly, rates start at $50 night and go up to only $120 for a stunning 2-floor “penthouse” suite on the top floor. Blue Cave is one of the West End’s best-kept secrets. Going to sleep in a castle to the immediate sound of crashing waves is a unique experience. Even if you don’t get to stay here, be sure to stop by the on-site Hideaway Eatery, owned and run by Chef Teddy, for a delicious lobster dinner.

On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

Rick’s is probably the most touristy spot in all of Jamaica, but there’s a reason it’s listed in 1,000 Places to See Before You Die, so don’t miss experiencing it at least once. Get there around 4 p.m. to avoid the crush of tour bus traffic that happens closer to sunset, then order a couple of cocktails—Rick’s serves up a myriad of options—and stake your claim on a prime viewing spot for the sunset and cliff-diving. Local divers swing from trees and drop into the surf or plummet from the surrounding cliffs, some of which rise more than 30 feet above the sea. Even the occasional tourist will brave the jump into the water below. A reggae band adds to the animated vibe. Lest you feel like just another tourist sheep at the sunset very-happy hour, console yourself in knowing that locals enjoy it almost as much as visitors do.

Aqua Nature Park, a well-maintained and verdant retreat 40 miles east of Negril, offers visitors a chance to take a dip and cool off in the Venture River. The river, which flows through a swimming hole on the property, has small, colorful fish and a cascade. Owner Steven delights in conducting walking tours of his family’s property, and can teach you quite a bit about the Jamaican plants and fruits he grows. (Don’t miss seeing the enormous cotton tree.) A casual restaurant and bar, with some reggae playing in the background, rounds this experience out into a lovely, low-key afternoon escape for couples, families, or anyone looking for a taste of real Jamaica.

If you only have one day in Lisbon, it has to be a perfect one. Enjoy the unique light of Lisbon and stroll around the neighborhoods and along the river. Listen to fados in a local tavern. And at the end of the perfect day, enjoy the sunset over the red rooftops of Lisbon while dining on fresh seafood.

From high-end shopping malls filled with high fashion and international brands to small shops stocked with made-on-site treasures and some of the world’s best bookstores, Tokyo is every shopper’s delight. Some of the best shopping districts include Ginza, Roppongi, Omotesando, Nihonbashi, Akihabara, and Nakameguro. For last-minute souvenirs for everybody on your list, head to Tokyu Hands Shibuya for 20 floors of merchandise ranging from kitchen wares to stationery and luggage.

For decades, Buffalo was home to several corner pubs and a handful of breweries, but as the population shrank, so did the bar count. Thankfully, with the city’s resurgence came a slew of local taverns, high-end cocktail bars, cozy coffee shops, and late-night clubs that, together, have created a better-than-ever drinks scene. From Elmwood Village to Hertel, there’s no shortage of places to imbibe in Buffalo these days.

Suddenly, grub that is both Chinese and Jamaican is a thing. Chef Craig Wong, third generation Chinese-Jamaican himself, has taken over a Dundas West space and done quite the number on the local dining scene, turning out a cuisine of his own that manages to encapsulate all that is Toronto. Pick from eats like the Jamaican patty double down — chef’s take on the famed KFC number — and the dirty fried rice with red sausage and peas. For a small group, go with the so-called Whole Shebang and test out Wong’s take on jerk chicken. Dinner can be reserved, but if you’s aiming for brunch, be there when the place opens and tuck into the Hong Kong-style waffles and the luscious maple butter French toast.

French Polynesia has so much to experience, it is hard to decide what is a must-do. You can swim, snorkel, and watch expert surfers in the azure waters; doze on a white-sand beach and wake for fresh-caught tuna and a Tahitian sunset; or sleep in blissful French Polynesian bungalows overlooking blue lagoons. These jaw dropping beautiful islands in the South Pacific offer endless possibilities—why not try them all?

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