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This colonial artifact overlooks the turquoise Indian Ocean and the Coast Line train that runs along it. Sights from the ocean-view rooms stretch to the city of Colombo, 20 minutes away. Trainspotters should request a room at the hotel’s north end to score a balcony with views of the ocean and the tracks. From $105, 94/(0) 11-271-1711, mountlaviniahotel.lk

Lemongrass restaurant is one of Oslo’s only Caribbean restaurants. Their food is inspired by the French, Spanish and British colonial history throughout the Caribbean, and they offer everything from bouillabaisse to jerk chicken and curried goat. Located next to Nasjonalgalleriet (the National Gallery) and just a stone’s throw from Oslo’s high street, it makes for a satisfying tropical meal when the winter cold sets in.

If you want to vacation like British royalty, visit the mosquito-shaped island of Mustique, which Naomi Campbell, Mick Jagger, and Princess Margaret have all called their home away from home. Once on land, there’s no better place to stay than the Cotton House, a private retreat that feels like the lap of luxury. Set on 13 acres of cerulean beachfront and gardens thick with jasmine and frangipani, the 20 rooms and suites are awash in neutral hues inspired by their surroundings, with wicker pendant lighting, ikat throw pillows, and breezy mosquito nets over the beds. Explore the coral reefs near the shoreline in a glass-bottom kayak, or improve your backhand with help from the resident tennis pro. After a day of sun-soaked adventure, dine on fresh-caught specialties (pan-seared barracuda, Caribbean-style sushi) at Veranda restaurant, then retire to the Great Room, a colonial-inspired lounge offering rare and local rums.

The Bo-Kaap was one of the few Cape Town neighborhoods to escape apartheid’s bulldozers—the cluster of bright buildings, once known as the Malay Quarter, housed many of the slaves who worked for the 17th-century Dutch colonialists. In this colorful area, you can also see some of the oldest, most beautiful mosques in the country, including the Auwal Mosque on Dorp Street. Upscale shops have been moving in lately, but don’t miss one of the originals, the spice merchant Atlas Trading Company. To go back in time, explore the Bo-Kaap Museum, furnished like the house of a typical 19th-century Muslim family.

The second-oldest museum in Australia, this is where you’ll learn about Tasmania’s Aboriginal heritage, its history since settlement and the island’s wildlife. There’s also a collection of Tasmanian colonial art. A spectacular redevelopment in 2013 opened up new public and exhibition spaces, making this an unmissable stop on any Hobart cultural tour. Admission is free, and there are free 40-minute guided tours Wednesdays through Saturdays.

At this luxury collection of six historic homes—some from the 16th century—guests can book a bedroom or an entire house, all within blocks of Santo Domingo’s most important attractions. You won’t find out which room or home you’ll be staying in until your arrival, but you’re sure to be pleased. Located in the heart of the Zona Colonial, the casas are exquisite. Two were part of former convents, one was a monastery, and another was once the private home of a famous Dominican fashion designer. Each one features unique decor and its own courtyard, and five of the six have private swimming pools. Upon check-in, you’ll receive a loaner iPhone to communicate with your house butler and the round-the-clock concierge team, who can help arrange excursions like culinary tours in the Old City and visits to one of the Caribbean’s largest organic cocoa producers.

Founded in 1519, In’t Aepjen is one of the city’s oldest brown bars (the Dutch version of an English pub), and the cozy room regularly draws a large crowd given its proximity to the main train station. It’s also curiously decorated with monkeys—monkey statues, stuffed monkeys, monkey posters—a nod to its name, which translates to “In the Monkeys.” The legend goes that sailors returning from the Dutch colonies were cash-poor, so they settled their bill with exotic pets (namely monkeys) acquired on their journeys. You’ll have to pay with euro, but the beer selection is decent and you can also try the local spirit, jenever.

Australia is world-renowned for scuba diving, but you don’t have to go all the way to the Great Barrier Reef or Ningaloo. Most people don’t know there is plenty of good diving in and around Sydney, too. One of the best sites is Magic Point off the tip of Malabar Headland National Park south of Maroubra. There’s an extensive reef system and large caves that are home to weedy sea dragons, stingrays, and a recovering colony of grey nurse sharks (which by most accounts are harmless to humans). Local outfitters such as Frog Dive Scuba Centres can lead you there.

Cattle Track is one of Scottsdale’s best-kept secrets. This clutch of 1930s adobe structures may be located in a typical residential neighborhood, but Cattle Track’s story as an artist colony is extraordinary. Fritz Scholder, an influential Native American painter, lived and worked here. So did sculptor Louise Nevelson. Philip C. Curtis, Cattle Track’s most famous artist-in-residence, went on to found the Phoenix Art Museum and was regarded as the dean of arts in Arizona. Today, artists of all types—painters, dancers, photographers, and even blacksmiths—set up working studios that can be toured for free Monday through Saturday.

You know how they say that Montreal is a happy mixture of North America and Europe? Well, if there’s one place in the city that’s truly unique, and not influenced by any other colony, it’s Plateau Mont-Royal. Located just a few minutes north of downtown, this neighborhood is lively, colorful, and somewhat eclectic. Here young families, hipsters, and fancy folk mingle together in harmony. In this iconic area you will find everything you need—from French bistros, typical French-Canadian brunch joints, clothing stores, and fine groceries. Nothing is expensive as such, but restraint is in order, because absolutely everything is enthralling!

The little town of Baie-St.-Paul has been a haven along the north shore of the St. Lawrence since the 1670’s, when the French began settling here. Today, just a couple of hours from Québec city by car, it’s an artist’s colony full of charming galleries and restaurants. I hadn’t been here in over a decade when I brought my wife here for her first visit. The dramatic Charlevoix region (the rolling landscape northeast of Québec city) was one of her favorite areas, and we spent an afternoon here, reveling in the cool green, soaking up the contrast from home in Arizona...

No one quite remembers when the hipsters started flooding into what is still a rather Kiwanis-club-style banquet hall for Mexico’s Spanish community, but they’re here to stay. Arts and media types, often in large, vociferous groups, favor the ground-floor cantina—a wide-open, too-brightly-lit space featuring a fabulous midcentury bar—where they rub elbows with domino-slamming old-timers. Yes, drinking is the big idea, but the menu of old-school Spanish fare (tortilla omelettes, croquetas, seafood, and pork dishes) is entirely serviceable, particularly after midnight when attendance peaks (it’s said it only closes after everyone clears out, almost always in the wee hours). Everyone who’s anyone claims to be “over” Covadonga, yet there they are, nightly, cutting up with beloved friends; keep your eyes peeled for genius writers you wouldn’t recognize anyway.

What do Al Capone and Bruce Willis have in common? They both did time here at Eastern State Penitentiary. (OK, Willis wasn’t an inmate, but he did shoot the film 12 Monkeys here.) The facility’s first inmate was brought through these doors in 1829, and the prison was in use until 1971. After closing, it became a target for vandals and housed a sizable colony of stray cats. Real estate developers proposed repurposing it as condominiums (high-security, of course), but preservationists won out. They raised funds to stabilize the crumbling interior and remove trees that were growing inside some cells. Wander through its stark interior and learn about the fascinating history of this unique site and its previous tenants, including Capone. Don’t miss the special art installations that are on display here all year round.

I don’t know whether it was the early morning fog, the rolling hills surrounding the vineyard, or the grapes themselves that made me do a double-take: Was I really in Chile’s Colchagua Valley, or was I back in California’s Sonoma Valley? With its intoxicating location and old world charm, Casa Silva (the colonial-style inn that sits in the midst of the family vineyard) has the best of both. It’s a place to relax, tour the surrounding vineyards, and – naturally -- drink their own varietals (especially the Sauvignon Gris, Sauvignon Blanc, and Petit Verdot). With only seven rooms, Casa Silva sits somewhere between a B&B and a guest house, with shabby chic rooms that are a throwback to Chile’s colonial era. We snagged room no. 4, with high ceilings and a comfy four-poster bed as well as an oversized bathroom. While the inn itself is special, the restaurant is worth a visit on its own. It has a clubhouse feel, overlooking the family polo field, but with unique and breathtaking views of the Andes. Hotel guests can take a leisurely 20-minute walk through the vineyard to the restaurant, which features Chilean specialties like conger eel, queso fresco, and tuna ceviche in one of the most dramatic settings I’ve ever enjoyed. (And don’t pass up the mote con huesillos, aka “wheat berry peach dessert.”) Finally, not to be missed: the tour of Vina Casa Silva, which houses one of Chile’s most up-to-date wine facilities and the family’s collection of perfectly restored antique cars.

One of the best coffee shops in the city, the Haas “Collective” (haas means “rabbit” in Afrikaans) has grown organically over the years to include not only coffee, but also design, art, and advertising. Formerly located in an old slave home in the Bo Kaap, Haas now takes up a refurbished colonial building in the city, where you can also have light meals at the plush yet relaxed venue. Selected artworks for sale include must-have gilded African bowls by Michou.