Isla de Providencia, Colombia
The residents of Providencia, a 25-minute flight from neighboring San Andrés Island, make much of their association with Sir Henry Morgan, the 17th-century swashbuckler de picted on rum bottles worldwide. As well they should: Only a 492-foot-long floating bridge separates Providencia from Santa Catalina, one of Morgan's favorite bases. A quarter-mile hike to the top of Providencia's El Pico yields 360-degree views of pristine rain forests and of the area where Morgan hid his loot. Near Aguadulce Bay, Hotel El Pirata Morgan's 27 rooms have private balconies, many overlooking the pool (011-57/8-514-8232, from $62). About four miles away at Playa Manzanillo, Roland Roots Bar hosts beach parties with reggae music and drinks served in coconut shells (no phone, from $7.75).
Comarca Kuna Yala, Panama
One of Panama's largest indigenous groups, the Kuna people have lived on the Comarca Kuna Yala chain of more than 350 islands and coral cays since the 1600s. Kuna women make and sell molas, swatches of hand-embroidered cloth in vivid purples, reds, and blues that are typically made into garments. The men spend their days fishing for grouper and mackerel and leading visitors on boat trips to the archipelago's dozens of uninhabited islands, some barely 100 yards wide. Many hotels here offer immersive, all-inclusive experiences. At Cabañas Uaguinega on Achutupu Island, 45 minutes from Panama City by air, the rate for a bamboo-walled, solar-powered cabin covers two tours or cultural outings daily and all meals (uaguinega.com, from $140 per person).
Water Island, U.S. Virgin Islands
To call Heidi's Honeymoon Grill a restaurant would be an overstatement—it's a food truck that parks on the beach and serves patrons seated at picnic tables—but it's about as close to an actual restaurant as you'll get on this 490-acre speck of land a 10-minute ferry ride from St. Thomas. Honeymoon Beach serves as the unofficial community center for Water Island's 161 residents, hosting Monday night golf-cart drive-in movies, Wednesday night bingo, and candlelit gourmet dinners catered by Heidi's on Saturday evenings (340/777-5288, $25). Most people stay in one of the more than a dozen vacation homes (vrbo.com, from $1,200 for a week).
Anegada, British Virgin Islands
The 32-mile Horseshoe Reef surrounds tiny Anegada, a low-slung coral atoll that's a 12-minute flight from Beef Island. What the reef means for travelers is a lot more than great snorkeling; it protects some of the longest beaches in the British Virgin Islands and has also netted 200-plus shipwrecks, ripe for divers' explorations. Pomato Point Restaurant, on the southwest shore, is known as much for its museum of shipwreck artifacts as it is for its swordfish and conch dishes (284/495-9466, entrées from $20). At the nearby Neptune's Treasure hotel, paintings of boats on stormy seas hang in the nine rooms, set about 150 feet from the water (neptunestreasure.com, from $95).
You could be forgiven a double take upon arriving at Terre-de-Haut, a 45-minute ferry ride from Grande-Terre, Guadeloupe: It's like a slice of northwestern France, with goats nibbling scrubby plants on the hillsides and a culture steeped in the ways of early settlers from Brittany. In the villages, fishermen still mend nets on their front porches, while women sell tropical fruit tarts (called tourment d'amour) from wicker baskets. Even the 12 guest rooms at Auberge Les Petits Saints are decorated with French antiques (petitssaints.com, from $131). But it's not all about old times—a cosmopolitan yachting crowd regularly drops anchor (and their swimsuits) at the west coast's Anse Crawen beach.
There's no need to worry about high-rise resorts blocking your view on this 13-square-mile island a 22-minute flight from Grenada; unwritten law forbids building a hotel taller than the average palm tree. Near Hillsborough, on the island's west coast, the appropriately sized Green Roof Inn rents six rooms and two cottages with Wi-Fi and sea-view verandas (greenroofinn.com, from $70). Carriacou is also known for the easy coexistence of cultural traditions passed down by both West African slaves and early 19th-century Scottish settlers. Ritual "big drum" dances remain a vital part of life here; they're performed for funerals and festivals, including the Carriacou Regatta, in which sailors race boats built according to old Irish and Scottish shipwrights' plans.
FLIGHT AND FERRY NEWS
In October, US Airways increased nonstop service from Philadelphia to Barbados, and JetBlue added flights from New York City to St. Lucia and Barbados. The same month, ferry company Bedy Oceanline launched new daily routes connecting those two islands with Grenada, St. Vincent, and Trinidad (bedytravel.com, from $90 round trip). For a full list of nonstop flights to the Caribbean, see our Nonstop Caribbean tool.