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The three floors of art on display at the Ogden, one of a handful of museums in the city’s off-the-radar museum district near Lee Circle, run the gamut from Clementine Hunter’s paintings of plantation life to Shelby Lee Adam’s photographs of Appalachia. The medium varies, but everything on display has some tie to the South.

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.

Affectionately called the First Lady of Waikiki, this grande dame opened in 1901. Its gracious architecture harks back to the sugar-plantation era and wraps around a courtyard anchored by a massive banyan. Pull up a chair under its spreading branches—or else a seat overlooking the ocean—and enjoy island-inspired fine dining. East meets West here with appetizers like Kona abalone bourguignon, tempura asparagus with Parmesan custards, and twice-cooked octopus with macadamia romesco. Entrée standouts include the miso salmon and Korean-fusion Beach Bim Bop starring fiddlehead ferns, kimchi Brussels sprouts, and Ali’i mushrooms from Hawaiian grower Hamakua. Save room for its tour-de-force finale: A “dessert tree” with small bites of everything from macarons to red-velvet cheesecake.

In the blink-and-you’ll-miss-it village of Volcano, on the slopes of Mauna Loa and just outside of Hawai’i Volcanoes National Park, are a handful of B&Bs and cottage rentals (see also Volcano Rainforest Retreat). Among the oldest—but no less charming for its 25 years—is Volcano Village Estate (previously known as Hale Ohia).


It’s a small cottage colony, with guest quarters scattered around a two-acre estate thickly carpeted in emerald-green moss and shaded by stands of soaring sugi (Japanese cedar) trees. The main house, a quirky Queen Anne style Victorian with a miniature turret and stone chimney that make it look like it was lifted right out of a children’s storybook, dates back to the 1930s when the manager of a sugar plantation built it as a summer holiday home. The gardens were planted by the same master landscape architects responsible for the Liliʻuokalani Gardens in Hilo (at one time the largest Edo style garden outside of Japan).


All guest quarters are sweetly decorated, in a largely Craftsman style with ceramic tiles and soft woods; some have pretty, stained-glass windows. But on a chilly Volcano night—and most of them are since the town sits at 4,000 feet—nothing is quite as romantic as curling up by the fireplace in one of the three stand-alone cottages, unless, of course, it’s sitting in the garden and watching the dazzling night sky, which is reason enough to stay on this side of the island.

The final stop before the Hana Highway, Pā’ia was once a plantation town; today it’s a boho enclave full of galleries, independent boutiques, lazy cafés, and a Tibetan Buddhist stupa (place of meditation). Stock up on fuel for exploring at Mana Foods: Like Doctor Who‘s TARDIS, this indie health-food store is bigger on the inside than it looks from the outside. (It also has a shockingly vast selection at reasonable prices.) Other highlights include Mahina, often voted Maui’s best boutique, and the funky soaps, jewelry, clothes, and Hawaiiana of Alice in Hulaland. Downshift at Baldwin Beach Park, the best for bodyboarding and swimming. Then drive out to Ho’okipa Lookout (before the Mile 9 marker) to marvel at the massive breakers in winter or advanced windsurfers streaking across the sea almost all year round.

Sister restaurant to local favorite Serpico’s in Upcountry, this sweet, welcoming spot serves New Jersey–style pizza in an old plantation-style house in West Maui. Tourists dine here, sure, but Prison Street isn’t overrun with overpriced rum cocktails or macadamia-crusted everything. Instead, the pizzeria keeps things simple with subtle nautical decor—a nod to Lahaina’s past as a whaling port—and thin-crust pies in variations like barbecue chicken, Philly cheesesteak, and the Windmills, a curiously named mix of Italian ingredients like pesto, mozzarella, and roasted red peppers. Also available are subs, salads, and calzones, all of which can be delivered if you need a break from dining out one night.

Martinique’s Route Des Rhums is something of the ultimate single island rum tour. The big reason for this being there are 10 different distilleries spread across Martinique’s 425 square miles! TEN! Two of the best are Distillerie Neisson and Plantations Saint James Martinique. All of them produce what’s called rhum agricole, but all you need to know is Martinique rums are the only rums in the world that have been granted the prestigious Appellation d’Origine Contrôlée (AOC) designation. Awarded by the French government agency Institut National des Appellations d’Origine (INAO) in recognition of the finest agricultural products (wines, cheeses, butters, etc), the AOC designation is an incomparable stamp of excellence in the culinary and spirits world.

Dasheene, the restaurant in the award-winning Ladera Resort, is a magical place unlike any other on the island. The open dining room, overlooking the sea, is so close to the Pitons that you feel as if you could reach out and touch the peaks. The menu, which focuses on ingredients sourced from local farms and plantations, puts a creative spin on classic St. Lucian cuisine, including plantain gratin with a coconut rum sauce, and roast conch. The restaurant is open for breakfast and lunch as well, but there’s no beating the romantic atmosphere and sunset views at dinner, which make a meal here well worth the high price.

A tour of St. Nicholas Abbey is a chance to explore one of the finest so-called great houses of Barbados. Not an actual abbey, the well-preserved Jacobean plantation mansion in the northern parish of St. Peter dates from the mid-17th century and is filled with antiques. On the mahogany tree–dotted manicured grounds, visitors can also see the old steam mill and rum distillery that are still in operation; the output from the latter, and other local products, are sold in the gift shop.

Manifiesto Café is known for its wide-ranging menu of coffees and careful brewing methods. Order a cup with beans grown in Mexico, Colombia, Costa Rica, El Salvador, or a handful of varieties from Europe. No matter which coffee you choose, it will be freshly-roasted. Manifiesto doesn’t serve coffee that was roasted more than 48 hours earlier. But that’s not the owners’ only rules for the coffee they serve. They also prefer beans harvested at plantations that are about 4200 feet above sea level. If you’re looking for a quick cup of coffee, go elsewhere. Manifiesto takes its coffee very seriously and uses a variety extraction methods. The payoff? Quite easily the best cup of coffee you’ve had in a good long time.

With its striking white facades and terra-cotta rooftops, you might mistake Cap Maison for a Mediterranean villa on the Costa Brava. However, this all-inclusive resort set on a former sugar plantation on St. Lucia’s north coast offers more than meets the eye. The pastel-hued interiors are matched by the sunny dispositions of the superb staff, who cater to every request, whether it’s finding a shady spot by the terraced pool area, booking a paddleboarding excursion off the private beach on Smuggler’s Cove, or arranging for the house yacht to take you to the neighboring island of Martinique for the day. Don’t miss the sunset views at the Cliff at Cap restaurant, where locally sourced dishes like reef conch ceviche and passion fruit soufflé are topped off with some of the resort’s house-made rum.

Near the northern end of Eleuthera, Coral Sands is one of the few hotels fortunate enough to sit directly on Harbour Island’s famous Pink Sands Beach, declared one of the world’s prettiest shorelines. Opened in 1968, the hotel has recently been updated in typical Bahamian style with bright colors and crisp whites, plus plantation shutters, soaring ceilings, and inlaid-wood furnishings with seaside themes. Public spaces follow suit: classic black-and-white tiles anchor the restaurant, where continental specialties are served beneath elegant plaster arches, and an open-air bar is backed by the island’s turquoise waters. Because the beach is protected by a barrier reef, its surf is hardly ever more than ankle-high, but swimmers find comfort in the heated freshwater pool.

Located across the way from Half Moon Resort, Sugar Mill Restaurant is set on the grounds of an old plantation. Couples and small groups dine at candlelit tables either on a covered terrace or out on the lawn, and the splashing of the mill’s waterwheel and the chirping of crickets are an accompanying sound track to the top-notch service and Caribbean fusion menu. Order a bottle from the well-stocked wine cellar, visible as you enter the restaurant. For special occasions, a private table beside the waterwheel can be reserved. (In the mood for a lighter, slightly more casual meal? A tapas menu is available in the restaurant lounge.)

Aruba’s Palm Beach is known for its powdery white sand, tranquil blue waters—and sprawling full-service luxury resorts. Just steps away, the intimate Boardwalk Small Hotel is a laid-back alternative. Owned and operated by Belgian twin sisters Stephanie and Kimberly Rooijakkers, who were born on the island and spent their childhoods here, 14 casitas are scattered on the grounds of a former coconut plantation and individually decorated: studio, one-, and two-bedroom spaces are outfitted with bright pinks, yellows, and aquas, fully equipped kitchens, air-conditioning, and private patios with their own charcoal barbecues and hammocks. Breakfast offerings range from the local (think tropical fruit and house-made arepas) to the luxe (bottles of champagne), and can be delivered to your casita or beachside palapa, but with no restaurant on site lunch and dinner is up to you.

Once a delicacy of Japanese royalty, shave ice went mainstream in the 1920s. The refreshing treat then crossed the Pacific with immigrants—workers bound for the sugar plantations and pineapple fields of Hawaii. Now a classic way to cool down in the islands, this sweet is more than a mere snow cone. Ice made from filtered water is shaved instead of ground, so the texture resembles a delicate snowfall in your mouth. Ululani’s goes a step further by using pure cane sugar and premium purees made in-house. Among its most popular blends are the Haleakalā (coconut and Leche topped with cream) and the Sunset Beach (guava, mango, passion fruit, and orange). The chain has six outlets around Maui, including one at the Hyatt Regency Maui Resort, and one in Kailua-Kona on Hawai’i Island.