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For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Off the coast of Port Antonio is a small, uninhabited plot called “Pellew Island,” otherwise known as “Monkey Island"--there used to be a colony of imported monkeys here. To get here, you could first head to San San Beach, a beautiful and private stretch open daily (10 a.m.4 p.m daily, US$5). Rent a kayak and snorkel gear and make your way over to the small plot, within clear view ahead. The island is completely covered in vegetation, there’s a small white sand beach, and the waters are shallow. Rest your kayak on shore and snorkel around the island for as long as you please. Visibility is incredible and this is one of the best snorkeling spots in the area. Just watch your step if you’re barefoot, as there can be sea urchins on the seabed.

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.

Looking for some peace and quiet? No need to stay in the heart of Seven Mile. Keep walking all the way north of the beach--or hop in a taxi--and end up at Long Bay Beach Park. Past the hotel belt, this stretch offers respite from the chaotic tourist scene. There are picnic benches and changing rooms on site. Adjacent is an excellent beach restaurant, Cosmo’s, in case you have the munchies. Few folks venture here and you’ll be relieved to know that vendors stick to the busier, crowded stretch of Seven Mile. If you’re looking for even more quiet, take a taxi ride to Half Moon Beach, just 10 minutes away--a private, stunning crescent shaped stretch where you can swim and spend the day as long as you’re buying lunch at their excellent, casual on site restaurant serving the fresh catch of the day.

Grand Turk’s oldest church was built in 1823. Set inland on the edge of Town Pond in the capital, the whitewashed building was constructed by the island’s Bermudan settlers. After a refurbishment that welcomed an organ to the loft, the red-roofed church was rededicated in 2011.

The parish church of Fatima is in a little hamlet called Aljustrel. It is just down the road from the Cova da Iria, Fatima. The three shepherd children were baptized there and there attended Mass with their relatives and neighbors.The baptismal font in which the three shepherds were baptized is just inside the door on the left side. There are pictures and some history in the alcove. The interior has a good deal of marble and is surprisingly large. The parish cemetery is just across the street from the church and the Marto children were first buried there. In 1951 and 1952, Jacinta then Francisco were interred at the Cova da Iria in the new Basilica as it was being built. Lucia, the eldest seer, was buried there in 2005. She died at 98 years of age at a convent in Coimbra, Portugal. Family members are buried in the parish cemetery. One of the children’s brothers, Joao who died in 2000 at the age of 94, is interred there. When I walked inside the walls of the cemetery, I could feel a stillness and calm quiet. This is a stop that adds another layer of history to the story of the miracle of Fatima. One of the best restaurants in the Fatima area, Tia Alice, is just across the street on Rua do Adro. I enjoyed local dishes and local wines at Tia Alice...... Delicious.

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.

Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

The hike up the Mayfield River to the waterfall nicknamed the Washing Machine requires walking in the river itself at times, and at one point, swimming through a tunnel. Along the way, you’ll be surrounded by lush fern trees and bamboo. You’ll need water shoes, a swimsuit, and a sense of adventure to take part in this, one of the best ways to see Jamaica‘s verdant interior. The trailhed is an hour’s drive from from Negril, and you’ll find lockers and a small restaurant there. Guides are always on hand to show you the way—you won’t make it without them, they know all the right places to place your foot. (Be generous with your tips—they may be having a great time, but this is their job.) The reward at the end of your hike? Two waterfalls. Swim underneath and feel the refreshing force of nature.

Go tubing on the White River with Ocho Rios Jamaica Tours and cool off in one of Jamaica’s most picturesque bodies of water. The jade colors of White River, dotted with fishing boats along its banks, rocks, and leafy banks, make it an ideal choice for shutterbugs and nature lovers. Combine your tube float with a stop at Irie Blue Hole, for a fun leap into the river-fed sinkhole.

Hop on a small barge-ferry to be whisked out to a larger boat for an unusual dinner on the water. Dine on the covered top deck, if you can snag a table, for an alfresco meal with a glittering night view of Montego Bay’s coast and the Caribbean. The menu is for seafood lovers but has options for everyone. The cozy, warmly lit nautical interior lends a relaxed and intimate vibe. Your fellow diners will most likely be locals, so you can feel like a Jamaica insider—previous passengers on the House Boat have included Steve McQueen, the Duchess of York, and the Beach Boys.

While Jamaica has several “great houses"—former plantation houses—the Rose Hall Great House, outside Montego Bay, is one of its most visited. Set on beautiful grounds towering over the Caribbean, this 18th-century Georgian home was once owned by Annie Palmer. While touring, you’ll hear the legend that tour guides like to tell—that Palmer, nicknamed the “White Witch of Rose Hall,” was a cruel slave owner who tortured and killed many of her workers, some of whom were her lovers, before eventually being murdered in her sleep. There’s no truth to that story, but it adds to the eerie atmosphere of the property. In fact, haunted house night tours of Rose Hall Great House are offered.

If you’ve ever longed for a ride down a river to spot crocodiles—and who among us hasn’t? [editor’s note: me!]—you can do just that on the Black River in southern Jamaica. The river cruises are a popular tourist attraction, but they never feel overrun. Enjoy an hour-long cruise past tall mangroves and ferns, spotting tropical birds and stopping when the guides greet crocodiles. The enormous reptiles swim right up and even open their jaws while passengers cringe and wonder if the guide’s hand is about to disappear. Don’t miss this fun chance to see some of Jamaica’s wildest interior.

For a refreshing swim, head to this deep mountain pool, which shines turquoise in the afternoon sun. On the upper reaches of the Hampstead River, the swimming hole even has a natural waterslide, fashioned from smooth, chafe-free rock. Pack and picnic and wear shoes suitable for the moderate rain forest hike in (1–2 hours roundtrip, depending on your route).