Extreme Caribbean Adventures
Intense Outdoor Activities Among the Islands
John Seaton Callahan / Moment / Getty Images
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.
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.
Guides can teach newbies how to ride the wind in this sport that combines elements of windsurfing, wakeboarding, sailing and parasailing.
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.
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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.
Shoal Bay, Anguilla
Once a secret hideaway, Anguilla has come into its own as a Caribbean hot spot for Hollywood starlets and honeymooners alike. Filled with beautiful beaches, posh resorts and overall laid-back charm, Anguilla's popularity is certainly well-deserved. There are 33 beaches on this 16-mile stretch of island, and the best part is that they are all open to the public. Shoal Bay is among the most popular with 2 miles of pearly-white sand on the Atlantic side that has a convenient equipment rental on-site for visitors.960 1280
Eagle Beach, Aruba
With miles of clean shores, tranquil waters and picture-perfect weather year-round, Aruba sees its fair share of tourism. Eagle Beach is one of the most beautiful beaches on the island with its wide swath of powdery sand and gentle surf perfect for swimming. The beach is a bit quieter than some of its neighbors, but still free to the public like all of Aruba’s beaches. Sleep across the street from these serene shores at the Dutch-influenced Amsterdam Manor Beach Resort.960 1280
Trunk Bay, St. John
Nearly 50 years after Laurance S. Rockefeller donated Trunk Bay to the National Park Service, the beach and offshore coral reefs remain among St. John's most breathtaking and well-preserved attractions. Trunk Bay's clear, warm waters and silky coral sands draw tourists in droves, and its well-maintained facilities include chair and snorkel equipment rentals and showers. Visitors can bask in the tropical sun, snorkel the 225-yard-long Underwater Trail of reefs, or try their hand at underwater photography -- the clean water and variety of colorful sea life promise spectacular photo opportunities.960 1280
Crane Beach, Barbados
Barbados is a distinctive island, both in its natural beauty and fun-loving culture. This West Indies gem is actually a coral island. The sandy beaches are made up of pulverized coral, which makes for fine, soft sand. Just off the coast, there are coral reefs that tempt snorkelers and scuba divers with their exotic underwater life. Crane Beach is known for its great waves, and the waters are filled with surfers and even some body surfers, though the rough waters are appropriate only for strong swimmers.960 1280
Palominos Island, Puerto Rico
Palominos Island is a 100-acre private beach getaway off the coast at the northeastern tip of Puerto Rico. Adding to the island’s allure is its air of exclusivity as it’s only available to guests staying at the El Conquistador Resort and Golden Door Spa. Those lucky VIPs board a fast-moving catamaran for an 8-minute ride to this retreat for a day of snorkeling, wind surfing or riding wave runners or embrace the island paradise by simply lounging in a hammock with a frozen cocktail.960 1280
Philipsburg, St Maarten
St. Maarten is a cosmopolitan beach destination with European flair on the Dutch and French sides of the island. Phillipsburg is the capital of the Dutch side and the island’s hub of activity with cruise ships coming and going and visitors strolling along the brick-lined Great Bay Beach Promenade. This busy beachfront runs for nearly 2 miles with colorful umbrellas dotting the wide sandy shores. For a completely different experience, head to Cupecoy Beach, a clothing-optional spot beneath golden sandstone cliffs.960 1280
While Nassau’s beaches are certainly lovely, the allure for many is the spectacular diving just off the sandy shores where visibility can reach up to 100 feet. Explore the Blue Hole, a natural hole 100 feet across and 200 feet deep full of large schools of fish. Trinity and Piece of Cake caves both have openings large enough to swim through and are home to some large lobsters. There are also countless shipwrecks that have occurred along the reefs surrounding the islands of the Bahamas that make for some very exciting underwater adventures.960 1280
Virgin Gorda, British Virgin Islands
The British Virgin Islands are made up of a collection of smaller islands, each with its own unique topography and island vibe. Virgin Gorda, 1 of the largest islands, is a popular tourist spot with posh resorts, pristine beaches and great sailing. Virgin Gorda is probably most famous for the Baths, a unique national park on the island's southwest coast with white sandy beaches framed by gigantic granite boulders, some of these with diameters reaching 40 feet. Bring along your water shoes, a snorkel and a waterproof camera and explore the series of caves and grottos created by these irregular boulders.960 1280
Harrismith Beach, Barbados
Spend the day like a castaway on the remote Harrismith Beach in the Parish of St. Philip in Barbados. Though it’s just a short walk from Bottom Bay, this sandy paradise is far removed from the resort scene at the more developed beaches. The beach is accessible by a flight of stone steps carved into a cliff overlooking the sea. The cliff-top ruins of an old plantation house add to the romantic air. After descending the steps to the shore, enjoy a picnic, search for shells or relax with a book—but swim at your own risk as there’s no lifeguard on duty at this hidden gem of a beach.960 1280
Horseshoe Bay, Bermuda
Bermuda's famous pink-sand beaches are considered some of the loveliest seaside retreats in the world, and the shores of Horseshoe Bay are no exception. Wide stretches of the pastel pink sand -- the result of crushed shells, coral and calcium carbonate -- offset by clear blue waves lapping at the shore, create an enticing lure for the scores of visiting beachgoers who descend each year upon the 21-mile-long island. Horseshoe Bay Beach's facilities, lifeguards and equipment rental shops have helped secure its ranking as Bermuda's most popular shore.960 1280
Best Caribbean Beaches 10 Photos
10: Hotel MaromaThirty miles south of the crowded Mexican resort of Cancun, in the heart of the Mayan Riviera, you'll find the pristine, quiet area of Maroma. The Hotel Maroma has a mere 36 suites decked in handmade mahogany and bamboo furniture. A stay here is worth every penny. 960 1280
9: Sandy LaneExperience this Caribbean resort for a haven of tranquility, a luxury romantic retreat or the perfect location for families looking for an endless list of recreational activities. Sandy Lane is a luxury golf resort with 3 golf courses: The Old Nine, The Country Club and the world-renowned Green Monkey. For a more relaxing getaway, we recommend guests head to the 47,000-square-foot Barbados spa that provides a wide range of massages, facials and body treatments. So go ahead and indulge yourself! 960 1280
8: AtlantisRising up majestically from the Caribbean is Atlantis, a resort based on the mythical city that sank without a trace 11,000 years ago. Along the 3 miles Cabbage Beach's sugary sand, guests can snorkel, parasail, jet-ski or just lounge to their hearts' desire. Then there is the Leap of Faith: a 60-foot drop down a Mayan temple water slide that takes you to 1 of the resort's spectacular family attractions -- the aquarium. 960 1280
7: Four Seasons Resort NevisThe tropical island of Nevis sits a balmy 19 degrees north of the equator. While it's only separated from other islands in the West Indies by 2 miles of warm water, go there and you'll feel a world apart. One of the most remarkable aspects of the Four Seasons Nevis is that it has attained a 5-diamond rating. Getting a five-diamond rating from AAA is hard enough in the United States, but to get this rating on a relatively remote Caribbean island is a testament to the resort's commitment to service. 960 1280
6: Ritz-Carlton St. ThomasSt. Thomas is part of the US Virgin Islands, just east of Puerto Rico. Blessed with breathtaking views, it's no wonder this island attracts tens of thousands of visitors each year. Combining Old World Colonial charm with a tropical setting, the 152-room Ritz-Carlton St. Thomas sits on 15 acres of impeccably manicured grounds and its stately elega nnce attracts guests from all around the world. 960 1280
5: Beaches Turks & Caicos Resort and SpaA visit to these beautiful islands will often cost you a pretty penny, but not if you stay at the Beaches Turks & Caicos Resort and Spa. Opened in 1997, this popular spot is an all-inclusive resort. 960 1280
4: Little Dix BaySet 90 miles off the coast of Puerto Rico, Virgin Gorda is 8 1/2 square miles of lush greenery and stunning crescent bays; it truly is a tropical wilderness. Little Dix Bay includes an amazing number of hiking trails and offers some of the best snorkeling in the Caribbean. 960 1280
3: Parrot Cay by ComoLocated 575 miles southeast of Miami, the 8 major islands and more than 40 keys of Turks & Caicos cover only a combined 196 square miles of sun-drenched shoreline. Stars like Paul McCartney, Demi Moore, Bruce Willis and David Copperfield have all said ahoy to this place. And unlike super-accessible mega-resorts, the exclusive 5-star Parrot Cay Resort and Spa can be reached only by small boat. 960 1280
2: Caneel BayThe island of St. John is a treasure trove of tropical jungle and enticing enclaves. It was once the playpen of gazillionaire Lawrence Rockefeller, who fell in love with this lush land in the 1920s. Caneel Bay facilities include 166 elegantly understated rooms, 3 restaurants, a 20,000-square-foot spa and a state-of-the-art tennis facility. 960 1280
1: Hyatt Regency, Aruba Resort & CasinoSet just 15 miles off the coast of Venezuela, Aruba is the westernmost island of the Netherlands Antilles. Here Spanish, Dutch and Caribbean culture blend as comfortably as your beachside cocktail. The Hyatt Regency Aruba is one of the region's premier resorts, because it has a lot of casual elegance and the staff combine that attribute with an incredible array of really fun activities. 960 1280
Top 10 Caribbean Resorts 10 Photos
BahamasA short 30-minute flight from Miami, the Bahamas’ proximity to mainland US makes it a convenient beach escape. Consisting of 700 islands in the Atlantic, the Bahamas provide much more to explore than just Nassau, the capital city that’s a popular cruise port. If you want to get away from the high-rise hotels and bustling crowds, head to the Bahamas’ Out Islands for secluded beaches and natural wonders. 960 1280
RoatanRoatan, the largest of Honduras’s Bay islands, is located near the second largest barrier reef in the world. With its prime location, Roatan is known as one of the world’s best scuba diving spots. Often called the Caribbean’s “best-kept secret,” Roatan’s tourism has increased in recent years, attracting more than just divers. The laid-back culture and uncrowded beaches make Roatan an appealing alternative to other Caribbean islands. 960 1280
ArubaOff the north coast of Venezuela lies Aruba, a popular island getaway with reliably sunny days. Outside of the hurricane belt, this Dutch island promises tourists plenty of beach days with its dry climate. Upscale restaurants and lively nightlife offer visitors plenty of options after a day of soaking up the sunshine. 960 1280
BermudaThis cluster of islands may not technically be part of the Caribbean but they sure feel like it. Bermuda is often dubbed the “Jewel of the Atlantic,” and rivals its neighbors in the West Indies as the perfect tropical island getaway. With pink-sand beaches, temperate weather and a unique fusion of British and African heritage, this is a place you’ll want to get lost in. 960 1280
Turks and CaicosLooking for a beach hideaway? Look no further than Turks and Caicos. Consisting of 40 islands and cays, 8 of which are inhabited, Turks and Caicos boast some of the most pristine beaches in the world. Lose yourself here in the turquoise waters and secluded white-sand beaches. 960 1280
Dominican RepublicOffering more than just beautiful beaches, the Dominican Republic’s diverse landscape includes 3 large mountain ranges, including the 2-mile-high peak of Antilles. A former Spanish colony, the Dominican Republic has a rich Latin culture as well as strong ties to America’s national pastime, baseball. More major league players hail from the Dominican Republic than any other country. 960 1280
BarbadosThe coral island of Barbados attracts tourists from around the world with its unique natural beauty. Coral reefs line the coast, offering incredible snorkeling and scuba diving opportunities. Visitors should also be sure to catch a meal that includes the national dish -- flying fish. 960 1280
Puerto RicoA US territory, Puerto Rico doesn’t require you pack a passport to visit its shores. With over 270 white-sand beaches, the Caribbean island begs to be explored. You’ll have the beach to yourself in Vieques, Puerto Rico’s “secret island.” This national wildlife refuge is just a 30-minute flight (or a short ferry ride) from San Juan. 960 1280
JamaicaJamaica is known for its strong African history more than any other Caribbean island. The island nation celebrates its vibrant culture through strong reggae beats and memorable jerk dishes. And don’t miss a chance to explore the island’s diverse landscape of mountains and rainforests. 960 1280
Caribbean Island Escape 11 Photos
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.
Hikers enter the first chamber of an intricate cave system, where more than 500,000 bats roost during the day.
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.
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.