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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.

Once called Hulk Bay after the prison ship that was moored here, the Sydney suburb is now known for stately homes and amazing harbor views. This appeared in the August/September 2013 issue.

A stunning bay with little development, Soliman Bay is great if you want to get away from it all. Head to Chamico’s for a delicious whole fried fish and a strech of sand all to yourself.

Opened in 2003, Carlisle Bay is set on a lush, isolated section of Antigua’s south coast and has a 21st-century design that feels more contemporary than Caribbean. With muted shades of grays, whites, and greens, the hotel projects an uncluttered, understated luxury. Its most remarked-on feature, though, is the way it appeals to both couples and families by keeping the two separate. Each group has its own cluster of rooms at its own end of the beach, and never the twain have to meet, except perhaps for lunch at Ottimo, the poolside Italian restaurant. The crescent of beach is tucked into a sheltered bay, so the waves seldom do more than whisper up onto the white sand, against a backdrop of forested hills. It’s all very restful, but the long list of free non-motorized watersports and the extensive kids’ club ensures everyone has plenty to do.

Old Québec can be a little hard on the wallets of budget travelers. It’s not that the restaurants are overpriced, but they definitely cater to the tourists who fill its streets most days, especially in the warmer months, and who are happy to pay a little extra for the location and the opportunity to enjoy a long meal savoring some Québecois dishes. Le Chic Shack is a good option, however, if you are looking for a quick meal that’s a good value. The restaurant’s gourmet burgers include beef, bison, chicken, and veggie ones, all served on brioche rolls. There are also three different choices of poutine—classic cheese, braised beef, and wild mushroom. Try the restaurant’s rendition of a milkshake, or lait frappé, spiked with Baileys, Kahlua, or whiskey if you are in the mood for something stronger.

Directly off the northern highway is Columbus Park, overlooking the scenic harbor at Discovery Bay, where Columbus was thought to have first anchored—although recent indications are that he sailed there from St. Ann’s Bay. The park is the only open-air museum in Jamaica, displaying artifacts dating back to Arawak times. Take in the glorious views, ideal for a photo op, and step back into a slice of Jamaica’s history.

Among the several art galleries along Main Road in Kalk Bay, Kalk Bay Modern displays a variety of art, jewelry, fabric, photography, and pottery from several different African countries, as well as an exciting collection of the works of South African aboriginal San artists.

Often called one of the world’s most beautiful beaches, Trunk Bay is a crescent of snow-white sand with a small green islet on the north side of the aquamarine lagoon. Part of the Virgin Islands National Park, Trunk Bay is known for its underwater snorkeling trail. Submerged signs along the trail describe the corals, tropical fish and other marine life found within the bay. Visitors can rent snorkeling gear on the beach, and lifeguards are in attendance.

Located along a stretch of coastline that’s sometimes called the birthplace of jerk cuisine, the Boston Bay Jerk Center is hard to miss. Various meats are cook on open pits using a technique that may explain why jerk never tastes so good at home: Uncured pimento logs are placed over a bed of hot coals, and the meat is laid directly on the green logs. The whole operation is then covered up by a sheet of corrugated zinc and cooked until it’s black on the outside and tender underneath. You can place your order by the quarter, half, or full pound. Don’t forget to add jerk sauce, which you can also buy by the bottle as a souvenir.

We were lying in the sand in Vieques. We’d been told to watch out for horses, but nothing could prepare me for this. What a majestic experience to see wild horses free on the sands of Sun Bay Beach.

Hout Bay is basically Eden. This ecological utopia has everything a nature lover could want, from imposing mountains and miraculous views (check out the Twelve Apostles range) to World of Birds, the largest bird park in Africa, home to 3,000 birds and over 100 walk-through aviaries. On weekends, you can shop for food and crafts at the lively market at the end of the harbor road. Besides Chapman’s Peak Drive, there are two other roads into Hout Bay, one from Constantia and another that passes the gorgeous surfer beach of Llandudno—also the exit for Sandy Bay, a nudist beach.

Nearby reefs and big boulders keep Bermuda’s beaches calm and colorful for snorkelers and swimmers. Both Tobacco Bay & Church Bay offer great snorkeling conditions along beautiful shorelines. With one in the east and the other in the west, you could combine a day of snorkeling and sunrise/sunset viewing. Tobacco Bay is located on the northeastern side of the island near St. George. This small cove of calm water protects a variety of parrot, clown, and other tropical fish. Tobacco Bay has a snack bar and equipment rentals, restrooms, showers, and changing rooms. When you tire of swimming with the fishes, dry off with a short walk to the historic site of Fort St. Catherine. Its eastern location makes Tobacco Bay a prime sunrise spot. Located along the island’s western side in Southampton, Church Bay is a local favorite for snorkeling. Tucked into a small cove within cliffs of coral, the reefs are close to shore and offer lots of small hiding spaces in which to discover tropical sea life. Just watch out for the jellyfish. Youngsters will enjoy exploring the tidal pools formed by the many rocks. Forget to pack your snorkeling gear? No problem. You can rent equipment from Church Bay Beach Rentals during the summer months. Sunset seekers should not miss this beach.

What started as a simple hat shop has grown over the years to a full-scale boutique with a wonderful range of women’s clothing from local designers. And you’ll find accoutrements such as scarves, gloves, bags, and umbrellas, stationery sets, coffee table books, cute odds and ends for the home, as well as children’s books and clothes. However, the hats still reign supreme—with fedoras, cloches, caps, and berets from hatmakers like Bailey, Christy’s, and Goorin Brothers.

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.

Kalk Bay Expresso is just one of several coffee shops in the quaint seaside town of Kalk Bay. The repurposed train car, which dates back to 1914, sets this restaurant apart. The cafe serves both sweet and savory crepes, making this the perfect stop for a mid-morning or afternoon snack en route while driving to see the sights on the rest of the Cape Peninsula.