Extreme Caribbean Adventures

The Caribbean offers more than just crystal-clear waters and white-sand beaches. Adventurous types of all stripes can find an extreme experience to suit their tastes.

Surfing School: Rincon, Puerto Rico

Rincon’s surf breaks hit the big time when the World Surfing Championships were hosted there in 1968. Now known as the "Caribbean Pipeline," this corner of Puerto Rico is the capital of the Atlantic surfing universe. Surfers will find waves to suit almost any mood, from longboard cruisers to 20-foot bombers. Breaks on Maria’s Beach, Tres Palmas and Domes Beach are favorites of pros including Kelly Slater.

Sass Global Travel is headquartered at the Rincon Surf School and will help you with every aspect of your expedition, including accommodations. 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 breeze 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 that sleep up to 8 guests.

MORE: Go Sailing and Kite Surfing with Kinga in the US Virgin Islands

Snorkeling With Humpback Whales: Silver Bank

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, and guides give instructions on how to approach the curious calves using slow, gentle movements.

The Aggressor Fleet offers weeklong expeditions departing from Puerto Plata, Dominican Republic, on the 120-foot Turks & Caicos Aggressor II, which sleeps up to 18 guests.

Canyoning: Dominica

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 cliffs into crystal-clear pools, wade, swim, climb and rappel through waterfalls.

Extreme Dominica’s canyoning tour lasts 3 to 4 hours and goes through canyons located near the capital of Roseau. All participants receive training, as well as a wet suit, 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 a 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 people's 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 or crawl — or maybe just float — in the most exquisite water on the planet? SwimVacation hosts swimmers of all abilities for weeklong 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, waterskiing, kneeboarding, wakeboarding, sand-castle building, shopping, hiking and napping.