THE FLORIDA KEYS
Why Go: The archipelago stretching off southern Florida is made up of 1,700 islands; when narrowing down which to visit, put Key Largo on the list so you can visit the only living coral reef off the mainland US. Key West is another must: there’s always something going on at Smathers Beach, from Jet Skiing to volleyball tournaments.
Where to Stay: Accessible only by boat or seaplane, Little Palm Island Resort & Spa offers luxurious castaway isolation. The quaint Marquesa Hotel, on the other hand, is set in Key West’s lovely historic district.
ST. MARTIN AND ST. MAARTEN
Why Go: It’s like visiting two countries in one on this sun-soaked, half-French and half-Dutch island. Thirty-seven beaches include Cupecoy and its dramatic sunsets; the windsurfing-friendly Orient Bay; and surfer spot Mullet Bay, where the beach scene is refreshingly tranquil. The Gallic influence on the cuisine in the gourmet hub of Grand Case makes the restaurant scene one of the best in the Caribbean, with Creole fish shacks, high-end French spots, and everything in between.
Where to Stay: The villas of La Samanna front the island’s largest beach. Bide your time in the casino at the The Westin St. Maarten Dawn Beach Resort & Spa between stretches of sunning.
Why Go: Maui offers some of the world’s loveliest drives, such as The Road to Hana, lush with rainforests and waterfalls, and a winding tour through Haleakala National Park to the world’s largest dormant volcano, with breathtaking overlooks along with the twists and turns. Wai’anapanapa State Park, not only consists of pristine waters and a black sand beach, but also stunning fresh water caves and cliffs crying out for jumping.
Where to Stay: The palatial Four Seasons Resort Maui is strewn with gardens alongside its beachfront property and many of its guestrooms include volcano views. The stylish Andaz Maui features a restaurant from Iron Chef Masaharu Morimoto.
TURKS AND CAICOS ISLANDS
Why Go: Only eight of the 40 islands in this archipelago are inhabited. Providenciales is the center; Grand Turk is the capital; and North and Middle Caicos are quiet getaway spots. Divers and snorkelers enjoy the show along the world’s third largest barrier reef, while Long Bay beach is the place to take up kite boarding. Blue marlin fill the surrounding waters, making the islands a great spot for fishing, too.
Where to Stay: Seven Stars Grace Bay includes a vast seawater pool and private cabanas on the beach. The entire island of Parrot Cay is devoted to the resort Parrot Cay by COMO, with its unspoiled mile-long stretch of beach.
BIG ISLAND, HAWAII
Why Go: The Big Island’s Kilauea is an active volcano that has been constantly erupting for the last 6 years; its glow alone transfixes tourists. The Waipio Valley and Mauna Loa Observatory trail are big with hikers for the overlooks and waterfalls. Pohue Bay is one of the world’s loveliest secluded beaches, and a favorite for nesting sea turtles. A tour and tasting at the Hawaiian Vanilla Company, the US’s first commercial vanilla farm, lends new appreciation for the sweet bean.
Where to Stay: The recently-restored Volcano House has a long history on the island, and is quite literally that—built into the edge of the Kilauea volcano. The golf course and spa are big attractions at the Fairmont Orchid Hawaii.
Why Go: Hawaii’s own “Grand Canyon,” Waimea, is a colorful, 10-mile-long and 3,500-foot deep gorge that visitors have to see to believe. Hiking the Nã Pali cliffs offers picture-perfect coastline views while Po’ipu Beach brims with activity and water sports. Those seeking seclusion love Kalapaki Beach. The gentle rapids of Kauai’s various rivers allow for fun, scenic, and mellow kayaking expeditions.
Where to Stay: The Grand Hyatt Kauai Resort and Spa is an Art Deco gem with a sprawling seawater pool. The renowned butler service in the top-category rooms and a new spa set the St. Regis Princeville Resort apart.
Why Go: The iconic Pitons—pointed, greenery-covered rock formations—command the skyline of this paradise. The best views are by boat; and be sure to bring a camera as this is one of the most photographed landscapes in the Caribbean. Jalouise Beach sits right between the Pitons and Anse Chastanet is the preferred beach for snorkelers. Thrill seekers zip through the canopy at the treetop Adventure Park.
Where to Stay: The rainforest location and plantation glamour make Sugar Beach, A Viceroy Resort a desirable stay. Boutique hotel Cap Maison favors a romantic Cliffside setting with captivating views.
LOS CABOS, MEXICO
Why Go: If you crave a little nightlife with your beach scene, you’re in the right place. The tequila flows at the Sammy Hagar-owned entertainment complex Cabo Wabo. And break out the binoculars from December through April for gray whale season. A boat ride around El Arco, a natural rock formation that resembles an arch, is a great idea for a sunset cruise.
Where to Stay: Hotel Las Ventanas Al Paraíso is known for making the travel experience effortless, from staff members unpacking guests’ suitcases to personalized cooking classes. Guests love the spa and the tri-level swimming pool at Cabo Azul Resort.
HONOLULU AND OAHU
Why Go: Paradise found is the beach in Kailua in Oahu, an expanse of white sand, gentle tides and several small islands within reach of an easy kayak paddle. The vibrant nightlife of Downtown Honolulu is a refreshing break from solitude. The famous Waikiki beach made its name on surfing and is a great place to hang ten. Diamond Head, heiress Doris Duke’s opulent Cliffside estate, is an architectural marvel worth a gander.
Where to Stay: The recently-renovated Halekulani is known for its spot-on personalized service details. Classic hotel The Royal Hawaiian dates back to 1927, and was the resort that put Hawaii on the map.
Why Go: Everything’s “irie” in one of the friendliest, mellowest islands in the Caribbean. Reggae music was born here, and Reggae Sumfest in Montego Bay draws music lovers from all over the world in July, while Dunn’s River Falls in Ocho Rios are always well worth the hike. Seven Mile Beach in Negril seems like an endless expanse of heaven. Stress glides off the body upon landing, making it the perfect place to unplug.
Where to Stay: Built into the cliffs of Negril, the Rockhouse Hotel is nestled in a private and picturesque cove. Oracabessa Bay’s GoldenEye was once the home of James Bond creator Ian Fleming.
Why Go: The three islands that make up this chain are Grand Cayman, Cayman Brac, and Little Cayman. Grand Cayman is where most of the action is, and home to a thriving food scene, with chefs such as Eric Ripert, Michael Schwartz, and Jean-Georges Vongerichten. Crescent-shaped Seven Mile Beach is a haven for sun worshipers and snorkelers. Get up close and personal with stingrays at Stingray City.
Where to Stay: Active sorts admire the tennis program, run by a former coach of Andre Agassi, and the Greg Norman golf course at the Ritz-Carlton Grand Cayman. Plantation-style Cotton Tree is hailed for its authenticity alongside modern amenities.
Why Go: Not just for spring-breaking college students, despite its reputation, there’s more than just the party in this part of the Yucatán. There are the ruins of Chichén Itzá, for starters, and El Rey nearby. The beach and open air restaurants at Playa Tortugas make it a great place to linger. To feel even more removed, remote Isla Mujeres sits just a ferry ride away.
Where to Stay: The Rosewood Mayakoba is perhaps the area’s most significant modern architectural landmark. Three pools, a spa, and a tequila bar add up to a winning formula at Maroma Resort & Spa.
PUNTA CANA, DOMINICAN REPUBLIC
Why Go: The Dominican Republic has the most Blue Flag beaches, which meet strict environmental standards, of the entire Caribbean. Of the ten beaches in Punta Cana, Playa Juanillo and Playa Punta Cana beach are among the favorites of frequent visitors. Waters full of dorado, wahoo, and marlin attract anglers while rappellers plunge deep into Fun Fun Cave and history buffs beeline to the House Museum of explorer Ponce de Leon.
Where to Stay: It’s all suites all the time at Meliá Caribe Tropical and the villas are designed by local hero Oscar de la Renta at Tortuga Bay Hotel.
Why Go: The fine, powdery white sand on the roughly 20 beaches edging this island include Eagle Bay, which even has free wifi, making it the ultimate remote office. Lovely Palm Beach always ends up on “top beach” lists and Arikok National Park has petroglyphs within caves from ancient cultures. There’s also a fair amount of wildlife: Pet a fuzzy nose at the Donkey Sanctuary and spy on some flyers at the Bubali Bird Sanctuary.
Where to Stay: It’s adults only at the Bucuti & Tara Beach Resorts, set on one of the island’s quietest beaches. The Hyatt Regency Aruba Beach Resort & Casino, complete with a kids’ camp and babysitting services, welcomes families with open arms.
SAN JUAN, PUERTO RICO
Why Go: The cultural offerings in Puerto Rico’s capital are unparalleled in the Caribbean—from the historic forts and cobblestoned streets in the Old San Juan neighborhood to the terrific collection at the Museo de Arte de Puerto Rico. The gold sand on Ocean Park beach provides a relaxing stretch for sunbathing while the big resort hotels line Condado Beach. Stand-up paddling in Condado Lagoon is all the rage. And don’t forget: no passport required for American citizens.
Where to Stay: Right in the middle of the historic Old City, Hotel El Convento is a perfect location from which to explore the enclave on foot. The Ritz-Carlton holds everything a luxury resort should, including a lovely beach, a casino, and high-end restaurants.
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