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Named after Dot Domilise and her daughter-in-law Patti, this shack-like corner shop on Annunciation draws locals and in-the-know visitors for some of the city’s best po’ boys. You can’t really go wrong whether you opt for the hot smoked sausage with gravy or “The Peacemaker” (half shrimp, half oysters). Either way, grab a Barq’s root beer and a stool at the bar while you wait for your sandwich and a table—they’re in short supply, especially during the lunch hour rush.

The Estate Whim Plantation Museum, billed as the only sugar plantation museum in the Virgin Islands, is set on magnificently landscaped grounds occupying 12 acres of what was formerly a 150-acre property. The restored early-18th-century buildings include a great house, fully restored windmill, and sugar-factory ruins that are open to visitors and can be toured alone or with a docent. Sugarcane still grows in one of the plantation gardens.

Located in a historic mansion on one of the oldest streets in Oranjestad, Bistro de Suikertuin is hard to miss. The building is painted a bright hue of yellow, reminiscent of the tropical birds that visit its namesake sugar garden, and the front porch features a blackboard with the daily menu. Tables are scattered inside and out, but the pretty garden is the preferred spot for savoring your morning coffee and Aruba’s traditional pancakes. Come lunch, the restaurant is all about salads, wraps, and broodjes (Dutch-style sandwiches with meat and/or cheese on baguettes). Note: Reservations are recommended for afternoon tea service.

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.

St. Lucia’s iconic twin peaks—Gros Piton and Petit Piton—dominate the island’s scenery, soaring 2,500 feet from the sea on the island’s southwest Soufrière corner. Designated a World Heritage Site along with the surrounding Pitons Management Area, these volcanic spires take every first-time visitor’s breath away. There are various ways to experience the Pitons. The brave hike either peak—Petit Piton is more strenuous, and the trail isn’t marked; Gros Piton has marked trails and is a two- to three-hour hike from the village of Fond Gens Libre. Others opt to take it easy and sail past them on a catamaran cruise, or view them from land along the coast or from the terrace of La Haut’s restaurant. Sugar Beach, facing Gros Piton, offers a frontal view of the peaks as you swim.

The Lobster Palace scores high on service, seaside ambience, and Caribbean charm. At this northwestern, coastal hotspot, the signature crustaceans are boat-to-bib fresh and served flambéed or pan-fried in massive portions. Note that, when the waves kick up and ground the fishing fleet, the restaurant can sometimes run out of lobster. Never fear, however, as the chef turns out other great dishes like tenderloin, moules frites, and shrimp in coconut sauce that are just as satisfying.

The Utah Brewers cooperative, a partnership between Wasatch Brewery and squatters craft beers, has an eye for where people drink. The latest proof: Wasatch Brew Pub, which serves playful beers (Polygamy Porter, anyone?) in a spot just off the new Sugar House plaza.

There are plenty of fancy doughnut shops. You know the type, the ones that count bacon or basil in their ingredient list. But if you’re looking for an old-school bastion of fluorescent lights and pink boxes full of fried dough, this is the spot. A family-run joint that has supplied prework breakfast and postbar bingeing since the 1960s, Bob’s draws a crowd day and night for the fresh doughnuts made from scratch. Bob’s bakes all the nostalgic favorites: glazed, chocolate, sprinkles, sugar, and fresh apple fritters, and crumb-topped doughnuts. You might also notice a giant doughnut in the window. Like a dare, this doughy beast invites you to take Bob’s Big Donut Challenge. Finish the beast within three minutes, and you’ll get your money back plus a Bob’s Donuts T-shirt and bragging rights, not to mention an inevitable stomachache.

A combination of train and bus, this three-hour tour weaves a fascinating route past some of the island’s most historic sights. Constructed from 1912 to 1926, the rail system originally carried sugar from St. Kitts’ estates to the factory in Basseterre, but today serves as a fun tourist attraction. Visitors ride in double-decker cars—the lower is air-conditioned, the upper open-air—past black-sand beaches, old plantations, and sugarcane fields, and then up a portion of Mount Liamuiga.

Like Five Guys in DC, Whataburger in Texas, and Shake Shack in NYC, In-N-Out is the West Coast burger joint for those in the know. It’s been a SoCal staple since it first opened in 1948 and has since developed a cult-like following throughout the Southwest. Order like a local off the not-so-secret-menu and either indulge with an “Animal Style” burger (extra pickles, extra spread, grilled onions and a mustard-fried patty) or pretend to be healthy with a “Protein Style” burger (gluten free with lettuce instead of a bun).

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.

Once a grand harem, this luxurious riad in the medina’s Andalusian Quarter is as enigmatic as its past. Interiors are peppered with worldly artifacts and contemporary furnishings, but all blend harmoniously with traditional handwoven rugs, bejmat tiles, and ornate lanterns. Seven lavishly chic suites are equally full of character: vintage Moroccan wedding shawls and antique Berber wardrobes offset modern amenities like high-end organic toiletries, walk-in rain showers and sunken stone tubs, and terraces wreathed in rose bushes and lush greenery. No less romantic is the hammam, complete with vaulted ceilings and graceful columns. There are also plenty of charming corners to settle into with a mint tea and homemade pastries, be it in the serene library courtyard, the umbrella-dotted rooftop lounge, or the hotel’s elegant crystal-chandeliered restaurant.

One of the most fascinating aspects of the BVI for beachgoers is the sheer array of sandy shores to explore. On Jost Van Dyke, the sand at White Bay skews more toward the white-gold end of the spectrum and gives way like piles of sugar beneath your bare feet. Hit the Soggy Dollar Bar to try the iconic Painkiller (a mix of rum, orange, and pineapple juices and cream of coconut, sprinkled with freshly grated nutmeg) in the place where it was invented. Just around the headland on the beach at Great Harbour, the sand skews slightly more golden, and the famed Foxy’s Tamarind Bar, another classic BVI watering hole, beckons. And for the most diamond bright, sugar-spun sands in the islands, make your way to Anegada, the northern and easternmost island in the BVI. Here, Cow Wreck Beach is a calm stretch with one mellow bar and a gentle slope of white sand leading to the water’s edge. On the far eastern end of Anegada, Loblolly Bay lures with an enticing crescent strand and a beach bar called Big Bamboo that serves up a mean piña colada, best enjoyed with a plate of conch fritters.

Okay, let me start by saying that I am not trying to ignite a war with fans of In-N-Out Burger or Shake Shack. But, if you come to D.C., Five Guys is your place for burgers—we don’t go in/out or shake a shack for our bite! Yes, the burger patties at the Five Guys chain are hand-formed and cooked atop a flat top griddle. Yes, they come sandwiched between the halves of a sesame seed topped bun. Yes, you can get them in two different sizes and topped with your choice of condiments. Yes, there are some awesome fries to go with it but only fries; there are no onion rings here. You should know that Five Guys prides itself on its fries. If you want to know the type of spud that gave birth to that day’s fries, check the chalkboard for the name of the farm and location. Unless you are really, really hungry and really, really love fries, go with the small order. It’s more than what most people can devour in one sitting! For the full Five Guys experience, order your meal at the counter and while you wait, munch on the free roasted, in-shell peanuts, but don’t eat too many! You need to leave room for that awesome burger that will soon make its way to you! There are various locations around D.C. (The first Five Guys restaurant opened in 1986 here in Arlington County, Virginia.) Check the website for the one nearest you and order online to beat the line.

Bypass the roadside watering holes and take a boat ride to Floyd’s Pelican Bar, instead. This thatched hut stands on stilts out in the water, making it a dreamy spot for an afternoon of swimming and shooting the breeze, solo or with friends. It’s 30 minutes from Treasure Beach (arrange a boat ride through your guesthouse or resort), and you can arrive for lunch and stay until after sundown for the just-caught fish, rum, and chilled Red Stripe on the menu. Inside the tiny shack, the flags of various countries hang and previous customers have left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon.