Surfing Expedition: Rincon, Puerto Rico
Rincon’s surf breaks hit the big time when the World Surfing Championships were hosted here in 1968. Now known as the "Caribbean Pipeline," this corner of Puerto Rico is the capital of the Atlantic surfing universe. Surfers will find almost any wave to suit their mood, from longboard cruisers to 20-foot bombers. Breaks on Maria’s, Tres Palmas and Domes Beach are favorites of pros like Kelly Slater.
Sass Global Travel offers week-long or 3-day expeditions that include a guide and unique accommodations in 3-story bamboo tree houses that poke through the top of the jungle canopy. Each tree house has its own kitchen, shower and solar electricity. Plan a trip between September and March for the best surfing conditions.
Open Water Kiteboarding: British Virgin Islands
For a unique kiteboarding adventure, try following the wind on a catamaran. You’ll be able to ride the wind coming from any direction and enjoy swells and slicks all to yourself. Guides can teach newbies how to ride the wind in this sport that combines elements of windsurfing, wakeboarding, sailing and parasailing. There is also plenty to do between sessions, such as snorkel, scuba, hike, tour or just kick back.
Sapphire Kite Tours offers 7-day trips departing from Tortola. Winter months bring strong trade winds averaging 20-25 mph to the BVIs, and most trips include sessions at Anegada, Virgin Gorda and Jost Van Dyke. Catamarans are known for stability in the water, speed and roomy interiors and sleep up to 8 guests.
Snorkeling with Humpback Whales: Silver Banks
Between January and March, humpback whales mate and calve in the Silver Bank, a region in the Atlantic between Turks and Caicos and the Dominican Republic. Snorkelers can slip into the water and swim with the majestic 10- to 12-foot calves as their mothers watch from below. Participants get close to the whales with inflatable rafts, where guides give instruction on how to approach the curious calves using slow, gentle movements.
The Aggressor Fleet offers week-long expeditions departing from Puerto Plata, Dominican Republic on the 120-foot Turks and Caicos Aggressor II, which sleeps up to 18 guests.
Canyoning, also known as canyoneering, abseiling and kloofing, is big in Dominica, where the volcanic rock is cut through by canyons and covered in cascading waterfalls. Adventurers get to jump over cascades into crystal clear pools, wade, swim, climb and rappel through waterfalls.
Extreme Dominica’s canyoning tour lasts 3 to 4 hours through canyons located near the capital of Roseau. All participants receive training and a wetsuit, helmet, life jacket and harness. Visitors with previous canyoning experience can sign up for an advanced trip that includes an overnight stay and a 270-foot waterfall.
Hike Into a Bat Cave: Trinidad
Trinidad’s mountainous terrain is full of animals, but travelers interested in a more extreme critter experience should look toward Mount Tamana, the highest point in the island’s Central Range. After a steep, 30-minute climb, hikers enter the first chamber of an intricate cave system, where more than 500,000 bats with wingspans of up to 1 foot roost during the day.
Visitors can choose to explore further into the second chamber of the caves, where more than 12 species of bats have been identified. At sunset, the group returns to the entrance of the caves to watch as a constant stream of bats flies within centimeters of peoples’ faces.
Long-Distance Swimming: British Virgin Islands
If swimming is your thing, why not take a vacation in which you can do the backstroke, butterfly, crawl or float in the most exquisite water on the planet? SwimVacation hosts swimmers of all abilities for week-long trips on a trimaran sailing yacht. Guests can participate in at least 2 guided, 1- to 3-mile open ocean swims daily, as well as stroke clinics with trained guides.
Non-swimming friends can enjoy lots of activities while based on the yacht as well, including snorkeling, water skiing, kneeboarding, wakeboarding, sand castle building, shopping, hiking and napping.
Travel writer Trisha Creekmore has been to more than a dozen Caribbean islands.