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21 Hottest Caribbean Escapes

Nothing says vacation like crystalline blue waters, white-sand beaches and luxurious indulgence. That's why we're counting down the 21 best destinations in the Caribbean, where vacation is a lifestyle.

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San Juan

San Juan

Roberto Cofresi aka El Pirata Cofresi was shot by a firing squad in San Juan, Puerto Rico. Confresi commanded a crew to attack primarily cargo vessels responsible for exporting gold. 960 1280
Port Royal

Port Royal

Pirate history buffs believe Port Royal, Jamaica, is a must-see Caribbean destination. It was once the pirate capital of the Caribbean. The British, based at Fort Charles, actively encouraged and even paid buccaneers based at Port Royal to attack Spanish and French ships in the 1600s. Fort Charles is the last of 6 forts that still exist as a tourist attraction. 960 1280

By Raychristofer (Own work) [CC BY-SA 4.0], via Wikimedia Commons  

Emerald Falls

Emerald Falls

Enjoy the lush surroundings of the Emerald Pool on Dominica, a famous pirate haunt in the Caribbean. Most of the movie Pirates of the Caribbean was filmed in Dominica and Nassau. 960 1280

goldistocks/Getty Images  

Aruba

Aruba

Aruba is a great place to watch the sun set while having dinner with the one you love, but you can also take a cruise on Aruba's Jolly Pirates Ships with the family. Get a quick pirate history lesson and enjoy snorkeling in old pirate hot spots. 960 1280

Wikimedia Commons  

Martinique

Martinique

Edward Low, one of the most brutal and vicious pirates in the 1700s, was hanged in Martinique. He captured over 100 ships, and he and his crew murdered, tortured and maimed hundreds of people. 960 1280

By Pascalou petit (Own work) [GFDL or CC BY-SA 3.0], via Wikimedia Commons  

Pirate-Themed Sailing

Pirate-Themed Sailing

You can't understand a pirate until you've sailed a mile on his boat. Take a cruise with Windjammer or Star Clipper, both offer pirate-themed sailing adventures. It's OK to drop anchor and take a swim, too. 960 1280
Port of Spain

Port of Spain

John Boysie Singh, known as 'the Rajah,' was born and later hanged in 1957 in Port of Spain, Trinidad, for the murder of his niece. Singh had a long career as a gangster and gambler before turning to piracy and murderer, terrorizing and killing 400 people on boats that traveled between Trinidad and Venezuela. 960 1280
Georgetown

Georgetown

Don an eye patch, down some rum and yell 'Ahoy, me hearties!' Hundreds of travelers head to the Georgetown harbor in the Cayman Islands for the Pirates Week Festival. The fun festival includes street dances, music, treasure hunts and parades. 960 1280

Noel Hendrickson/Getty Images  

New Providence

New Providence

Several years ago, we're sure pirates passed by this entrance to the Nassau harbor in New Providence, Bahamas. New Providence was a haven for nefarious pirates including Charles Van, Calico Jack Rackham and Edward Teach aka Blackbeard. A walking tour in Nassau is a great way to explore real pirate history. 960 1280

By Bryce Edwards from San Jose, CA, USA (Bahamas GazeboUploaded by Tomer T) [CC BY 2.0], via Wikimedia Commons  

Sunken Shipwrecks

Sunken Shipwrecks

Several tour companies and cruise lines offer shipwreck tours or snorkeling excursions to travelers who want to explore sunken ships in key Caribbean destinations, including Aruba, Roatan Island (Honduras), Buck Island (St. Thomas) and Barbados. 960 1280
Bahamas

Bahamas

A 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

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Roatan

Roatan

Roatan, 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

Getty Images/ Gail Fletcher  

Aruba

Aruba

Off 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

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Bermuda

Bermuda

This 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

Verena J Matthew  

Cayman Islands

Cayman Islands

A diver’s dream destination, the Cayman Islands offer world-class scuba diving and plenty of outdoor adventures for the active traveler. Hike through the 200-year-old Mastic Trail, swim in Stingray City or walk along the stunning Seven Mile Beach. 960 1280

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Turks and Caicos

Turks and Caicos

Looking 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

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St. Thomas

St. Thomas

Only 31 square miles, St. Thomas is considered the most cosmopolitan of the US Virgin Islands. Escape the island’s bustle and head to Magens Bay, hailed by National Geographic as one of the most beautiful beaches in the world. 960 1280

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Dominican Republic

Dominican Republic

Offering 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

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Barbados

Barbados

The 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 Rico

Puerto Rico

A 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

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Jamaica

Jamaica

Jamaica 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

  

Underwater Adventure

Underwater Adventure

Let the adventure begin! Take an underwater submarine tour to see Grand Cayman’s marine life, including a close-up view of colorful coral canyons, fish, sponges, stingrays, turtles and on a rare occasion, a shark. 960 1280

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Catamaran Cruise

Catamaran Cruise

Take a catamaran cruise! Sample the local Caymanian cuisine, while enjoying awe-inspiring views of the sea and the island. 960 1280

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Snorkeling in Stingray City

Snorkeling in Stingray City

Go snorkeling in Stingray City, a series of shallow sandbars found in the North Sound of Grand Cayman. Tourists visit the popular attraction to pet and interact with southern stingrays. 960 1280

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Horseback Riding

Horseback Riding

Go horseback riding along the tranquil blue waters of Grand Cayman’s pristine beaches. Some tour companies offer a fun trek through the island’s tropical forest and the beach. We suggest horseback riding along the beach to watch sun set. 960 1280

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Blue Iguana

Blue Iguana

Explore the wildlife on Grand Cayman Island, including the endangered Blue Iguana, the longest-living species of lizard. These blue creatures have been known to live up to 69 years near dry forests or near the shore. At least 5 non-profit organizations are working with the government to ensure the survival of the Blue Iguana. 960 1280

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Pedro St. James National Historic Site

Pedro St. James National Historic Site

Rebuilt after a fire destroyed it in 1970, the Pedro St. James house -- also known to locals as “the Castle” -- is where island’s first 400 residents met to elect the Caymans’ first legislative assembly, on December 5, 1831. Tourists can take a self-guided tour the house and get an awesome panoramic view of the sea. 960 1280

Adam Sowers, Flickr  

Seven Mile Beach

Seven Mile Beach

Seven Mile Beach aka West Bay Beach has been called one of the finest beaches in the Caribbean. This wonderful white-sand beach stretches from George Town to Long Point. Its sandy bottom and calm, clear water make it an ideal spot for families with small children. Seven Mile Beach is great for snorkeling and other watersports. If you’re looking for a spot to relax in silence, then steer clear of the areas located near the big resorts if you’re looking for a spot to relax and unwind in silence. These areas tend to be crowded. 960 1280

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Fishing

Fishing

Grand Cayman Island is a prime spot for fishing. Enjoy fishing with the family or book a more adventurous, deep-sea fishing trip to catch a blue marlin, mahi-mahi, wahoo or tuna. 960 1280

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Cayman Turtle Farm

Cayman Turtle Farm

More than 500,000 people visit Cayman Turtle Farm each year. It’s the Cayman Islands’ largest land-based tourist attraction. Jump in and swim with Green Sea Turtles and other colorful marine life in Turtle Lagoon; enjoy swimming and sliding down Turtle Twister Water Slide; and get a up-close and personal view of sandbar sharks, nurse sharks, tarpon and barracuda. 960 1280

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Wreck of the Ten Sails Park

Wreck of the Ten Sails Park

Step back in time and visit the park dedicated to the Wreck of the Ten Sails. On February 8, 1794, a convoy of 10 ships -- on its way from Jamaica to the US and Britain -- wrecked on reef. Two hundred years later, Queen Elizabeth II visited the spot and dedicated a memorial plaque and park (pictured) to remember the lives lost as a result of the shipwreck. 960 1280

Lhb1239, Wikimedia Commons  

Queen Elizabeth II Botanical Park

Queen Elizabeth II Botanical Park

Take a stroll through the lush Queen Elizabeth II Botanic Park, located off Frank Sound Road. While taking a nature walk, tourists may spot native wildlife, including chickatees, freshwater turtles, anole lizards and blue iguanas. 960 1280

Lhb1239, Wikimedia Commons  

Rum Point Beach

Rum Point Beach

Remote Rum Point Beach is located on the North Sound, along the northern coast of Grand Cayman. This beach has changing facilities, public toilets and showers on site and it’s a great spot for swimming. We suggest visitors grab a drink at Wreck Bar & Grill on a Sunday. Locals usually stop by in their boats, adding to the bar’s lively, but fun atmosphere. 960 1280

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