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When in Kingston, make time for a stop at Devon House, a grand 1891 Georgian mansion that was built for George Stiebel, Jamaica‘s first non-white millionaire. The lovely upright house and its 11 surrounding acres are now protected as a National Heritage Site, but that doesn’t mean that there’s not fun to be had. The sprawling grounds include shops, restaurants, a bakery, and a popular ice-cream shop, I-Scream. House tours can be arranged, but the grounds, landscaped with stately palms and fountains, are the highlight—it’s a great spot to take a stroll, read, shop, or dine. The mansion and its manicured lawns are also used for weddings and lavish events.

Along the southern coast, Treasure Beach is about as peaceful as Jamaican beaches get. A few well-known guesthouses and resorts are located in this fishing community, but you’ll probably see more locals than tourists around, especially when compared with the rest of the island. The black-sand beaches, teeming with shorebirds, are attractive, and happily there’s not much to do but catch the breeze, mingle with local families, and enjoy fresh seafood.

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

An often overlooked fishing village located just 10 miles south of Negril, Little Bay’s small, crescent-shaped shores and white sands will tug at your inner beach bum. There are a couple of local guesthouse options in these parts, and not much else happening within walking distance—except a slice of daily Jamaican life and some sea activities such as kayaking and snorkeling off the nearby reef. Bob Marley loved Little Bay so much, he had a house here and wrote lyrics from this beach. It’s an easy day trip from Negril and a nice spot for shutterbugs.

If you’re looking for a unique fine-dining experience under the stars, away from tourists and with gorgeous night skyline views, look no further than Robbie Joseph’s Seahorse Grill. Tucked on the grounds of the Montego Bay Yacht Club, this restaurant is popular among expats and residents and remains a best-kept secret. Classy yet unpretentious, it offers outdoor, waterfront dock, and terrace seating and “global cuisine with a twist of West Indian flair.” From a juicy steak night—hard to find in Jamaica—to pastas and Jamaican seafood specialties, you’ll be talking about that dinner under the stars for a while to come. The cocktails are pretty fabulous, too. This restaurant is a west coast gem.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

The west coast of Jamaica doesn’t sleep. If it isn’t some daytime live tunes on the beach, or a street party in the wee hours, it’s the evening live Reggae available in multiple seafront venues. At night, the island takes on a different energy and everyone comes out to enjoy the fresh air and the tunes. Almost every other Jamaican seems to have a natural talent for music. It’s no wonder, then, that there are plenty of local acts to go around, often performing covers of Bob Marley, from MoBay to Negril. Recording artists also show up regularly--from Beenie Man to Beres Hammond. Along the highways and neighborhoods streets are the latest posters, flyers or billboards announcing upcoming live Reggae shows. When in doubt, head to Pier One in Montego Bay, or Alfred’s, Bourbon Beach and Jungle Nightclub in Negril. Better yet, ask the locals, who love their music. The sound of Reggae is never too far off.

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.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

Jamaican food is not all jerk and meat patties! You can sample one of the island’s most popular snacks, pepper shrimp, along the south coast. In the town of Middle Quarters, roadside vendors cook the shrimp in big steaming pots on outdoor grills. The shrimp, caught in the Black River, are boiled in salty water and then spiced with chopped scotch bonnet peppers, sea salt, vinegar, and black pepper. Plastic bags of the fiery little shellfish are peddled to drivers passing on their way home from work and to lucky tourists for a messy and addictive snack.

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.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

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.

Goldeneye, to be clear, is not an easy place to leave. The land—the former home of Ian Fleming, where he wrote each of the 14 James Bond thrillers that would cement his place in literary and cinematic history—sits next to the tiny town of Oracabessa, on the northern coast. A warm, blue-green lagoon curls from the ocean around a small island and then lets out into a bay. You can look one direction and see a jungle, then turn around and see pristine white sand.

Blackwell bought the property in 1976 as a vacation home and a space to entertain family and friends but later he decided to transform it. In 2016, Goldeneye debuted a jumble of new huts, arranged around a small cove, a short walk from Fleming’s house and the resort’s original villas. The huts vary in height, designed to capture cooling breezes and allow guests to forgo air conditioning. And, crucially, they’re much cheaper to book than the Villas. Which is key because, up until this point, if you wanted to plan a visit to Goldeneye, you needed to either know Blackwell personally or have the excess capital to shell out potentially five figures on a vacation. (Part of the resort’s enduring gravitational pull is that many of the celebrity guests check both boxes.) With the beach huts, Blackwell has expanded, once again, the ambition of his famous resort.