Guadeloupe: Pedal Like the Pros
Professional cyclists from around the world meet on this butterfly-shaped isle for the annual Tour de Guadeloupe, a 797-mile, ten-stage road race. The race comes to the island in August, but you can ride the circuit any time (call Dom Location, 011-590-88-84-81, for a map and bike rental, $10/day). Or ditch the bike and explore the island's offroad attractions: black-sand beaches, jungle waterfalls, and the short hike through clouds of sulfur to the top of La Soufrière volcano.
St. Barthélemy: Buff Enough to Surf
The curl at the out-of-the-way (and, unofficially, clothing-optional) Anse de Grande Saline beach is the island's best for bodysurfing. The half-mile-long stretch of white sand on the south shore is a 15-minute walk and worlds away from the Hollywood types at St. Danjean Beach. Call the St. Bart's Tourist Office, 011-590-27-87-27.
Cuba: Total Immersion
Wheel through Havana with the local biking club. Hone your underused salsa moves. Debate hot political issues using your newly mastered verbs (like derrocar—to overthrow). All this and more on a two- to four-week crash course in Spanish language, Cuban culture, and island adventure. Call Cuban Outreach Tours, 415-648-2239; www.seca.org/ioc.
St. Lucia: Climb the Big Piton
St. Lucia's lush, volcanic twin peaks tower over sunbathers on the beach below—but why sit around in the shadows? Though local foresters have tagged precipitous and overgrown 2,461-foot Petit Piton off-limits due to falling rock, the summit of 2,619-foot Gros Piton begs to be topped, and the 2.5-mile trek can be done in four hours. Call the St. Lucia Forestry Department, 758-450-2078, for maps and information.
Trinidad: Walk with the Animals
Hike past the Lagon Bouffe Mud Volcano and two miles up a forest path, where howler monkeys, peccaries, and orange-winged parrots await you in the Trinity Hills Wildlife Sanctuary—a private preserve owned, interestingly enough, by a local oil company. To visit, call the Incoming Tour Operators' Association of Trinidad and Tobago, 868-633-4733.
Jamaica: Raft the (Other) Rio Grande
Play Huck Finn for a day on a guided, seven-mile run down the Class I water of the lower Rio Grande in the jungly Blue Mountains. Your craft: a 30-by-6-foot, hand-hewn bamboo raft. The highlight: chatting with rural Jamaicans—and Red Stripe vendors—along the riverbank. Call Valley Hikes, 876-993-3881.
Martinique: Absalon, Absalon!
Bushwhack through the rainforest, rappel down a 40-foot cliff, navigate a boulder field, and then slip into the 90-degree, orange (from the iron in the rocks below) waters of the Absalon Thermal Spring. Call Aventures Tropicales, 011-596-75-24-24; www.aventures-tropicales.com.
Jost Van Dyke: La Vida Coco
Watch the sun set over White Bay and grab a painkiller (Pusser's rum, Coco Lopez, multiple juices, and the obligatory nutmeg) at the self-serve Stress-Free Bar (284-495-9358) on Jost Van Dyke, a three-square-mile dot in the British Virgin Islands. Then pick up a guitar, bongos, or an empty coffee can and jam into the night with the eclectic house band. (Bonus: There's a campground out back.)