St. Bart/Anguilla/St. Maarten

Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.

Built on the site of an ancient Jewish synagogue that was abandoned in 1781, this building was the governor’s home before becoming the headquarters and retail shop for the famous Sint Maarten Guavaberry Emporium. Like the building, Guavaberry has a rich history and is a historical folk liqueur (there are even folks songs and stories written about it) that today is an important symbol of St. Maarten and the local culture. The product itself is high quality, made with fine, oak-aged rum, cane sugar, and rare wild Sint Maarten Guavaberries found at high altitudes in the center of the island. Once produced, the liqueur emits a woody, bittersweet, and spicy, yet fruity flavor. Sint Maarten Guavaberry Emporium also sells a number of other high-quality rums and liqueurs, as well as a wide range of hot sauces.

Situated on the Atlantic, Dawn Beach is renowned for its crystal waters and namesake sunrises. The waters are great for snorkeling, as the visibility allows you to clearly see more tropical fish than dreams provide. The Westin Dawn Beach Resort and Spa, St. Maarten sits on the shoreline, which means you’re never too far from a delicious meal or strong Caribbean cocktail. Maarten.

At Orient Bay Beach, visitors can alternate between lounging on soft, white sand, photographing the surrounding mountains, cooling off with a swim in the warm turquoise waters, and taking in aerial beach views while parasailing. For those who want an even tan, this is a clothing optional beach, although very few visitors actually go nude.

At Carousel Gelateria Bar, they craft authentic Italian gelato made with natural ingredients imported from Italy (except, of course, for the fresh island fruits). Watch how it’s made for a lesson in true Italian food culture, and enjoy the specialty dish: the Carousel Sundae, made with creamy chocolate, fresh island fruits, and whipped cream. Of course, the selection here is endless: classic gelatos, homemade ice cream sandwiches, sundaes with the works, sorbets, crepes, pastries, handmade cakes, and, if you’re thirsty, thick shakes and even alcoholic beverages. Once your taste buds are satisfied, take a spin on the whimsical merry-go-round or go for a walk in the waterfront hibiscus gardens. Sharon Pruitt/Flickr.