CARIBBEAN VACATION IDEAS
Insiders' Guide to the Caribbean
Whether you've been to these 10 Caribbean islands once or you're planning your fifteenth visit, we've got the inside scoop on some of the best must-see spots in the islands.
San Juan is still numero uno in Puerto Rico, but folks have increasingly begun gazing about 40 miles east—to Vieques. The nearly four-year-old W Hotels resort here has lured celebrity chefs (Alain Ducasse) and guests (Angie Harmon, Ryan Phillippe). But what's drawing more casual types, however, is Vieques's laid-back personality. Hospitality veterans Robin and Marsha Shepherd left their villa-rental business in St. Bart's to open the 10-room Malecón House in 2010, amid a row of mom-and-pop inns (maleconhouse.com, from $175). The most impressive and least crowded of the island's beaches (some of which have hit worldwide top 10 lists) are part of the Vieques National Wildlife Refuge, on land the U.S. Navy used as a target-practice center until 2003. Today, it's managed by Puerto Rico's branch of the Fish and Wildlife Service. "If it hadn't been for the Navy and Fish and Wildlife," says Bill Barton, who owns Vieques Sailing (787/508-7245, daylong boat trips including lunch $110, late Feb.-Oct.), "the east end would look like Atlantic City."
Sitting all alone in the Atlantic Ocean 650 miles east of North Carolina, Bermuda is a true outlier. It's not anywhere near the Caribbean Sea, and its food, architecture, and customs are far more British-colonial than tropical paradise. Still, the island (actually an atoll) has found an easy alliance with its neighbors to the south, sharing in tourism efforts and reaping the benefits of their counterbalanced seasons: The Caribbean booms in the winter, while peak season in Bermuda runs from spring through fall. Though Bermuda is always pricey—four of the five most expensive destinations in the Caribbean are here—visitors traveling now will find lower airfares, reduced golf fees, and hotels that are more than 40 percent off summer rates. It's not quite sunbathing weather: December days average 70 degrees. But it's perfect for touring the island's cultural attractions. Two years ago, Bermuda celebrated the 400th anniversary of the settlement of St. George's Town, the 350th anniversary of Warwick Academy, the oldest school in the western hemisphere, and the 200th anniversary of the Bermuda Post Office. Even the hotels have history: The 202-year-old main house of the Greenbank Guesthouse & Cottages incorporates cedar beams that were used as ballast in transatlantic trading ships (greenbankbermuda.com, from $145).
The Caymans are practically synonymous with two wealthy pursuits: deep-sea diving and offshore banking. Dive 365, an initiative launched by the islands' Tourism Association, is hoping to make at least one of those more accessible to regular folks (divecayman.ky). The project's goal is to establish and maintain one Cayman dive site mooring for every day of the year, which meant adding 79 sites to the existing 286 by the end of 2012. One of the most noteworthy additions is the decommissioned U.S. naval ship Kittiwake, a 251-foot submarine rescue vessel that now sits in 62 feet of water off Seven Mile Beach (kittiwakecayman.com, scuba pass $10, snorkel pass $5). "The Kittiwake has a history that divers can relate to, with recompression chambers and lots of bulkheads to explore," says Nancy Easterbrook of Divetech, a local dive shop that helped to prepare the vessel for her sinking in January 2011 (divetech.com, two-tank boat dives $120). "Because the top is only about eight feet below the surface, you can snorkel the wreck too," she says. Affordable hotels on Grand Cayman are rare, but one good pick is 130-room Sunshine Suites, just a stone's throw from the Ritz-Carlton; each room has a fully equipped kitchen (sunshinesuites.com, from $167).
The Dominican Republic is a great place to find affordable all-inclusives, particularly in Punta Cana, on the island's east coast. But along the north shore—famous for its sporty adventure culture—more intimate hotels and house rentals offer a worthy alternative. In Cabarete, the Residencial Casa Linda villas look more like a neighborhood than a resort, though all rental units come with daily housekeeping service (casalindacity.com, two-bedroom villas from $120). The villas are only five miles down the road from Iguana Mama Adventure Tours, which offers trips to the 27 Falls of Damajagua, known for daredevil-quality jumps and slides over the waterfalls (iguanamama.com, full-day tour $89). In recent years, north-coast outfitters have seen an increase in the popularity of—and the competition for—canyoning and cascading excursions. One new arrival, Monkey Jungle Dominicana, located between Cabarete and Sosúa, stands apart for its philanthropic bent (monkeyjungledr.com, zip line from $50). All the profits from its zip-line and suspension-bridge tours go to the free on-site medical and dental clinic, which is staffed by volunteers and treats patients who cannot afford health care. Kitesurfing may be Cabarete's most popular outdoor pursuit, and while there's no shortage of local instructors to show you the ropes, it's almost as much fun just to watch the theatrics from the waterfront Nikki Beach lounge (nikkibeach.com, cocktails from $7)—drink in hand, of course.