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Dinner at Le Toiny Restaurant is a full frontal assault on the senses; as if the spectacular ocean-side setting were not enough, the culinary witch doctors at Le Toiny, led by executive chef Jean-Christophe Gille, whip whimsical French classics into contemporary Caribbean masterpieces with just the right amount of gusto. Le Toiny is open daily for breakfast, lunch and dinner, and features the Tuesday Fish Market, and the Sunday “Brunch du Toiny.”

The 112-room Surfjack Hotel channels 1960’s Hawaii, with vintage upholstery on the headboards, reed ceilings, and midcentury modern furnishings. The onsite Swim Club, with its outdoor pool bar, hosts music events and movie nights. Don’t miss a meal at Mahina & Sun from celebrated Honolulu-born chef Ed Kenney, whose menu showcases island cuisine and ingredients, or a trip to the Olive & Oliver boutique, whose clothing and accessories line are inspired by Hawaiian culture.

Locals love the Sunday Supper at City House, when chef-owner Tandy Wilson serves his highly creative Italian-influenced menu, but you really can’t go wrong any night here. Wilson, a 2016 James Beard Award winner, is a Nashville native who spent time in Italy and California before opening his restaurant in the former home of a sculptor in the trendy Germantown neighborhood. Since then, he’s been drawing visitors and locals alike with his belly ham pizzas, corn bread gnocchi, and main dishes like roasted chicken and corn meal–crusted catfish with peppers, garlic, anchovy, lemon, and parsley. Those in the know bookend their visits with a perfectly crafted cocktail at the bar and a dessert from pastry chef Rebekah Turshen, like the almond ricotta skillet cake with lemon marmalade and lemon ricotta gelato.

Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay.

Deep in the wilderness about an hour’s drive north of Kingstown, Dark View Falls cascade off a cliff and into a pair of natural pools, where everyone gathers to swim in the crisp, clear water. The hike to the falls takes only about 10 to 15 minutes, but involves crossing a jungle-style bamboo bridge across the Richmond River. After passing through a clearing in a picturesque bamboo grove, you’ll arrive at the first fall, where you’ll find a gazebo, changing room, picnic area, and viewing platform for enjoying the beautiful scenery. Another short, more difficult walk will take you up to the second fall, directly above the first.

A two-minute ferry ride from St. Vincent’s Villa Beach brings you to Young Island—the first of the Grenadines. Here, the Young Island Resort welcomes guests and visitors alike to its beachside restaurant for casual breakfasts, local curry buffet lunches, prix-fixe dinners, and barbecue parties. Seated in an open-air hut surrounded by tropical flowers, you can dine on local specialties like freshly caught fish and lobster while enjoying the ocean breeze. Whatever you order, pair it with the restaurant’s signature bread, which comes in banana, coconut, cinnamon, white, wheat, and raisin varieties and gets sliced tableside right before your eyes. Just know that reservations are required to eat here, no matter the time of day.

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.

Vesper Bar at The Cosmopolitan is our favorite spot for a serious Old Fashioned—or Elderfashioned, the house’s riff, which gets a dose of St. Germain.

Milliner Mona Strand makes hats for the rich and famous - and for anyone else who would like one. The Philip Treacy of Oslo, Mona Strand has made hats for the Crown Princess of Norway and regularly holds exhibits in many parts of Europe. Her hats also appear on stage, on TV, and in film productions. She makes bespoke hats (appointments needed) and sells ready-to-wear hats in her shop in cosy area St. Hanshaugen.

Locals all agree this is the home of Zurich’s—perhaps Europe’s—best sausage. What they’re divided on is which is better, the St. Galler bratwurst or the Servelat—both superbly juicy, flavorful, and with excellent snap—and divine with a crusty bürli roll and super spicy mustard. After a two-year renovation (during which the grill operated out of an airstream trailer nearby), the original 1963 location reopened its doors in 2013 with roomier, more modern digs.

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.

Along with the beautiful scenery, parents will appreciate the many amenities that make Bermuda’s beaches the perfect place for beach bums of all ages. Lifeguards, gentle water, and nearby facilities are always a welcome sight for parents of small children. Clearwater Beach, on the eastern end of the island, has clear, shallow water and a 36-acre public park with restrooms and a playground. Picnic facilities, shade trees, and gentle water make Shelly Bay a good choice for the smallest of surfers, swimmers, and shell seekers. Horseshoe Bay Beach has lifeguards, showers, restrooms, and a nearby café. John Smith’s Bay, Elbow Beach, and Somerset Long Bay are more great beaches for families with kids.

Contemporary art can sometimes be pretentious or obscure, but DHC/ART adds an edgy sense of wit, with exhibitions ranging from the visual puns of Ceal Floyer to the exuberant portraits of John Currin. 451 rue St.-Jean, (514) 849-3742.

Albertha Grant never set out to win a James Beard Foundation award and win the adoration of international magazines and patrons—she simply cooked good food and served it to people in her North Charleston neighborhood. But amidst the last decade’s gold rush around Charleston cuisine, Bertha’s shines in both its authenticity and flavor. It’s a classic soul food joint, with daily meat-and-three specials like fall-off-the-bone fried chicken, sumptuous pork chops, and collard greens that perfectly balance savory and sweet (there’s plenty sweet in the ice tea for everyone). The neighborhood is predominately African-American, and locals still line up here for lunch along with out-of-towners and Peninsula-based workers seeking Southern food done right. The late namesake’s daughters and granddaughters run the counter-service place now, efficiently taking orders to keep the line moving on busy weekdays.

Rugged Monhegan, aka the Artists’ Island, lies about a dozen miles out to sea, and is reachable only by passenger ferries. About 60 hardy souls live here year-round, most making a living from the sea. If you get a sense of déjà vu when visiting Monhegan, it’s likely because so many of the island’s icons and vistas have been painted by American masters, including Robert Henri, Rockwell Kent, Jamie Wyeth, George Bellows, Edward Hopper, James Fitzgerald, Andrew Wyeth, Alice Kent Stoddard, Reuben Tam, and William Kienbusch. Artists and art lovers come in summer; bird-watchers flock here in spring and fall. Hiking trails access remote rocky beaches and craggy headlands. Go for the experience, the art, and the hiking, and don’t miss the museum at the lighthouse.