The Caribbean, with more than 700 gorgeous islands, is the perfect spot for a winter vacation. December to April is the best time to visit, and yet, you can go year-round and find beautiful weather too (it’s a little more of a gamble during hurricane season from August to October, but you can still get a sunny and hot week). Scattered across the Caribbean Sea, the islands are close enough to make it the world’s premier holiday spot for cruising, but still so different, that it’s sometimes hard to choose one over another. Here are a few pointers to help you choose between them.
Best Caribbean Islands | The Most Beautiful Beaches
Anguilla: You can choose between more than 35 gorgeous beaches, but the most popular are Shoal Bay East, Meads Bay, and Maundays Bay.
Aruba: Eagle, Palm, and Manchebo Beaches are amazing stretches of white powder sand beaches with crystal clear water.
Cayman Islands: The Seven Mile Beach is a world-renowned beach that’s in fact 5.5 miles long. And there’s a lot more white sand beaches to discover.
Cuba: Cuba’s Playa Paraiso Beach is one of the top 25 beaches in the world according to Trip Advisor. There’s also the splendid Playa Sirena Beach, with its glistening fine white sand bordering the clear Caribbean Sea.
Dominican Republic: Bavaro Beach, Macao Beach and Cayo Arena are all among the top 25 beaches in the Caribbean according to Trip Advisor. Their golden sand beaches are surrounded by gin-clear water.
Grenada: Besides the divine Grand Anse Beach, Sandy Island is totally irresistible with its snow-white sand beach and its turquoise water.
Guadeloupe: A lot of natural lovely beaches dot the island. Most of the best beaches lie between Gosier and St-François on Grande Terre.
Martinique: The beauty and the incredible diversity of the Martinique beaches are simply amazing: they come in a range of colors from the luminous white sand to the deep black of the volcanic beaches.
St Lucia: Reduit Beach is charming with its fine golden sand and its stunning views across the bay to double humped Pigeon Island. There’s also Pigeon Island, an extremely picturesque little strip of golden sand.
Turks & Caicos: Surrounded by the world’s third-largest coral reef, the Turks and Caicos Islands have some of the finest powdery-sand beaches and most ethereal turquoise seas in the world.
Virgin Islands (US): The pristine sandy beaches and tall palm trees under the bright cobalt sky make this an amazing place to bring your family or travel alone, including some of the best beaches in the world.
Best Caribbean Islands | The Best Dining
Anguilla: Anguilla is an island whose people are dedicated to great eating. It’s renowned for its 5 Star, super high-end restaurants.
Barbados: Barbados offers an impressive selection of delightful restaurants that rival some of the largest metropolitan areas in the world.
Cayman Islands: Grand Cayman has a reputation for some of the best food in the Caribbean. From charming roadside BBQ to beachfront fish shacks to international superstar chefs, the island has you covered.
Curacao: Curacao’s restaurants run the range from elegant dining to roadside kiosks, with just about everything in between.
Grenada: The restaurants of Grenada offer a wide selection of epicurean adventures. From continental cuisine to ethnic restaurants, to local cafés with full-on Grenadian delights, the flavors of the island are sure to leave you wanting more. Many of the restaurants are situated right on the beach, giving visitors a great view to enjoy while they dine-especially if they’re there at sunset.
Guadeloupe: Guadeloupe restaurants offer possibly the best gourmet dining in the Caribbean. With a fine blend of French raffinement and the hearty, spicy tropical flavors of the Caribbean, Guadeloupe food is a highlight of any trip to the French Indies.
St Martin: Although most people come to St. Maarten/St. Martin for sun and fun, they leave praising the amazing cuisine. On an island that covers only 37 square miles, there are more than 400 restaurants from which to choose. And according to one of our readers who are now living there, Kate, St. Martin has so much more to offer, like “the natural pools on the French side that you can take about an hour hike around the mountains to get to, out of Guana Bay“.
Best Caribbean Islands | The Best Snorkeling
Cayman Islands: The Cayman Islands has some of the best snorkeling in the world thanks to the calm seas, clear water and beautiful coral reefs close to shore.
Grenadines: Its clear turquoise water is perfect for snorkeling and you will see many different species of fish, corals, and sponges.
St Lucia: When it comes to Caribbean snorkeling, St. Lucia is one of the region’s often overlooked gems: it offers pristine coral reefs teeming with sea life, and many of these are right off the coastline.
Turks and Caicos: The Turks and Caicos islands have lots to offer if you’re up for checking out the undersea life in some of the world’s most crystal clear turquoise waters.
Virgin Islands (British): Snorkelling in the BVI is one of the most stunning pleasures that residents and visitors have to enjoy. The sights of the world beneath the water transport snorkelers to a seemingly unexplored universe full of wonder and mystery with strange and exotic creatures.
Virgin Islands (US): St John is one of the top Caribbean destinations for snorkeling. With arguably the best shallow water snorkeling in all of the Virgin Islands – you’re sure to have an awesome experience.
Best Caribbean Islands | The Best Diving
Bahamas: The Bahamas offer an array of dive experiences like no other destination in the world. You’ll find sunken Spanish galleons, inland blue holes, underwater caves and forest-like coral reefs teeming with vibrant marine life.
Bonaire: Bonaire’s pristine reefs and amazing diverse marine life are unique to the Caribbean. Because the waters around Bonaire are designated as an official marine park, diving Bonaire is like diving the Caribbean the way it used to be – untouched and unspoiled.
Cayman Islands: The Cayman Islands have three world-class dive destinations that have attracted scuba divers since scuba diving was invented. Known for amazing wall dives, beautiful coral reefs and visibility that often seems infinite, the Cayman Islands offer some of the best scuba diving in the Caribbean.
Dominica: This Caribbean island is a dive travel paradise, with take-your-breath-away topside and underwater sights.
St Lucia: St. Lucia boasts a number of stunning dive sites that pull divers into a tranquil world filled with secret nooks waiting to be explored. With some of the most captivating deep sea wildlife in the Caribbean, you can experience an underwater carnival as you swim amongst schools of brilliantly colored exotic fish.
Tobago: Prepare yourself for a wild ride when you dive the reefs of Tobago. Divers find in Tobago top-notch reefs and marine life, ranging from tiny tropical fish to massive manta rays, and drift diving with the Guyana is spectacular.
Turks & Caicos: The Turks and Caicos Islands are surrounded by one of the most extensive coral reef systems worldwide, and are consistently ranked as one of the premier diving destination.
Virgin Islands (British): There is such a variety of dive sites in the BVI that every day you are able to explore yet another aspect of the BVI’s unique topography.
Best Caribbean Islands | The Best Golf
Barbados: Barbados is indeed a golfer’s paradise with several exquisite existing golf courses and several more being developed.
Dominican Republic: With 26 golf courses to choose from, the Dominican Republic is rapidly becoming the premier golf destination in the Caribbean.
Grenadines: The Grenadines Estate Golf Club stretches over 150 acres of seaside landscape with half of the golf course lying on flat coastal plain and the other carved out of the cliffs above the bay.
Jamaica: With more championship golf courses than any other Caribbean island, no matter your level of ability, it will not be difficult to find a course suited for you. Give in to the seductive pull of Jamaica golf courses with their lush, tropical scenery and top-notch facilities.
Kitts & Nevis: St. Kitts & Nevis’ three golf courses include a gorgeous 18-hole championship course on Nevis, plus a splendid 18-hole championship course and a 9-hole course on St. Kitts.
Puerto Rico: Puerto Rico has a wide range of courses, both stunning and not so lovely.
Best Caribbean Islands | The Best All-inclusive Resorts
Antigua: Antigua offers a lot of luxury all-inclusive resorts scattered all along the gorgeous coastline.
Bahamas: Out of all the Caribbean islands, the Bahamas have one of the widest ranges of hotel and resorts; there is something to satisfy everyone here.
Dominican Republic: The Dominican Republic is one of the best Caribbean destination for the perfect all-inclusive resorts: luxurious, amazing beaches and service like no other.
Jamaica: Located mainly on the north shore, Jamaican offers world-class resorts: romance, luxury, and incredibly good dining.
St Lucia: Most all-inclusive resorts on St. Lucia are clustered in the north, starting in Castries and spilling into nearby Rodney Bay. If you’re after great dining and nightlife, consider staying in this area. Looking for total relaxation? Check out the resorts along the western shoreline.
Best Caribbean Islands | The Best Nightlife
Aruba: The nightlife of Aruba is dazzling and diverse: you can enjoy live music on the many terraces of bars and restaurants in Aruba; you can dive into a pub. But you can also taste the typical Aruban atmosphere in a local bar, a ‘rum shop, jump on the dance floor in the nightclubs and discos, or try your luck at the casinos in Aruba or endless salsa dancing.
Bahamas: When the moon lights up the night sky, the entertainment world awakens in The Bahamas. Throughout the islands, you can find quaint bars serving up our traditional Goombay, Junkanoo or Rake & Scrape music, as well as New York-style nightclubs and everything in between. Enjoy a tropical Bahamian cocktail while you try your hand in a casino, or enjoy the sounds of live music in a bar or club. And, on some islands, you can sit on a beach and watch a bonfire under the full moon.
Cayman Islands: Cayman Islands nightlife is largely centered around the Georgetown and Seven Mile Beach areas on Grand Cayman. Seven Mile Beach begins just north of Georgetown, so it’s easy to travel between the two destinations if you want to get a taste of the nightlife on both sides.
Dominican Republic: The Dominican Republic offers fabulous nightlife experiences for all tastes: from beach parties and bars with live music where you can dance all night, to cozy spots where you can relax and maybe enjoy the country’s most famous beer, Presidente.
Jamaica: When the sun goes down, Jamaica comes alive. With reggae beats, live music and dancing on the beach ‘til dawn, join in swaying to the rhythm.
Puerto Rico: Puerto Rico is the nightlife capital of the Caribbean; Puerto Ricans were born to party. In Old San Juan the Salsa vibes last into the wee hours. For a less hectic atmosphere, the Santurce area and the Condado-Isla Verde strips are ideal.
St Maarten: Sint Maarten is the Caribbean’s nightlife island with 14 casinos and countless bars and discos.
Trinidad: Trinidadians take their entertainment very seriously. As Trinidad’s cosmopolitan population has grown more affluent, nightlife and entertainment choices have grown to meet the growing demand, with a range of settings and activities to keep you entertained all night long.
Virgin Islands (British): The BVI offers a wide variety of entertainment, especially live music.
Best Caribbean Islands | The Most Relaxing Islands
Anguilla: On Anguilla, the sounds of the gentle turquoise sea and the soft winds through the palms provide natural relaxation and reprieve. The island is a breath of fresh air and a place to feel natural, beautiful and relaxed.
Aruba: Many visitors say that Aruba is the most relaxing place they’ve ever been. There’s something about the warm, dry air and cooling trade winds that help people unwind.
Barbados: The natural environment of white sandy beaches, clear blue seas, cool breezes and swaying palm trees forces you to unwind and relax.
Grenada: Quieter than many of its island neighbors, Grenada takes this approach one step further and is even regarded as having a relaxed pace of life by the residents of neighboring Caribbean countries.
Guadeloupe: The Guadeloupe beaches are many, so finding one to suit your taste and preference won’t be hard. Some of the beaches in Guadeloupe feature little more than sand and palm trees and are perfect for relaxing.
Turks & Caicos: The Turks & Caicos Islands offer a variety of great resorts where relaxation is the primary focus.
Virgin Islands (British): The British Virgin Islands host numerous superb remote beaches, or “bays.” Standouts include Brewer’s Bay and Long Bay on Tortola, and Mahoe Bay and Savannah Bay on Virgin Gorda. But the truth is, just about any BVI stretch of sand will bolster the “get-away-from-it-all” mentality.
Best Caribbean Islands | The Best Hiking
Dominica: In Dominica, every trail across the island leads you to discover nature’s pristine environment with a touch of adventure, through gorges and valleys, into dense mountain rainforest, from rushing streams and rivers to natural springs and bubbling mud baths, to a myriad of cascading waterfalls, and a vast array of flora and fauna.
Dominican Republic: Walking or hiking trips through the various national parks in the Dominican Republic can include anything from seeing protected desert areas, to mangrove swamps and forests, to cave networks that display Taino Indian art (done hundreds and thousands of years ago), to nature preserves with hundreds of different species of birds, reptiles and other tropical fauna.
Grenada: The most popular area in Grenada for hiking and trekking is undoubtedly the rainforest around the Grand Etang Forest Reserve, high up in the mountains of the island’s interior. The trek is excellent!
Guadeloupe: The Caribbean called Guadeloupe “Karukera,” island of beautiful waters, and considering all the hot water springs and tall tumbling falls, it was aptly named.
Jamaica: The Blue Mountains in Jamaica is a hiker’s paradise. You have to see it to believe it… the flowers and flora, the birds and animals.
Martinique: Land of hiking, Martinique welcomes the lovers of nature over 130 kilometers of marked out paths. Long strolls along the Atlantic and Caribbean coasts, Mont-Pelée ‘s ascent, diving in the exuberant nature of the inland hills, waterfalls… more than thirty itineraries are waiting for the amateur or skilled hiker.
Puerto Rico: Puerto Rico’s mountainous interior offers ample opportunity for hiking and climbing, with many trails presenting magnificent panoramas at the least expected moments. There are also awesome beachfront and coastal trails around the island.
St Kitts & Nevis: On a paradise island in the Caribbean, there lies a tricky peak that makes for a grueling climb.
St Lucia: St. Lucia’s dramatic terrain provides many hiking trails through the island’s rainforest reserve.
St Vincent & the Grenadines: Whether you feel like a short, easy stroll or want the challenge of a more strenuous trek, St.Vincent has something for you. Rewarding destinations include picturesque rivers and superb waterfalls such as Dark View Falls and Trinity Falls, as well as forest hikes such as the Vermont Nature Trail and the Cumberland Nature Trail.
Tobago: Tobago’s landscape ranges from beaches to rainforest, with a variety of levels of difficulty to its hiking trails. From the unspoiled Main Ridge Forest Reserve to trails along swamps and rivers, Tobago’s terrain provides excellent hiking.
Virgin Islands (US): St. John USVI will delight both the serious hiker and the casual walker. The Virgin Islands National Park maintains several exciting trails including the famous Reef Bay Trail. There are also gut walks, scrambles, and short trails to interesting and out of the way places.
Now I thought of listing for you ALL the Caribbean islands meeting some specific criteria.
Best Caribbean Islands for Body Surfing
Anguilla, Antigua and Barbuda, The Bahamas, Barbados, Martinique, Puerto Rico, St. Lucia, Sint Maarten, St. Martin, Trinidad and Tobago
Best Caribbean Islands for Camping
Anguilla, Antigua and Barbuda, British Virgin Islands, Cuba, Dominica, Jamaica, Martinique, Puerto Rico, St. Lucia, St. Eustatius, Trinidad and Tobago, U.S. Virgin Islands
Best Caribbean Islands to play at a Casino
Best Caribbean Islands for Cave Exploration
Best Caribbean Islands for Helicopter Tours
Best Caribbean Islands for Parasailing
Best Caribbean Islands for River Rafting
Best Caribbean Islands for Rock Climbing
Best Caribbean Islands for Submarine Tours
Best Caribbean Islands for Tubing
Best Caribbean Islands for Turtle Watching
Best Caribbean Islands for Volcano Excursions
Best Caribbean Islands for Waterskiing
Best Caribbean Islands for Whale or Dolphin Watching
Best Caribbean Islands for Zip-Line or Treetop Touring
Caribbean Islands Languages
English Speaking Caribbean Islands
Anguilla, Antigua and Barbuda, The Bahamas, Barbados, Bermuda, British Virgin Islands, Cayman Islands, Dominica, Grenada, Jamaica, Montserrat, Nevis, Saint Lucia, St. Eustatius, St. Kitts, St. Vincent and the Grenadines, Trinidad and Tobago, Turks and Caicos and the U.S. Virgin Islands
French Speaking Caribbean Islands
Haiti, Guadeloupe, Martinique, Saint Barthelemy and St. Martin
Spanish Speaking Caribbean Islands
Cuba, Dominican Republic and Puerto Rico
Dutch Speaking Caribbean Islands
Aruba, Bonaire, Curaçao, Sint Maarten
So whatever your choice among those wonderful Caribbean Islands, there’s no way you can go wrong! Each of them has so much to offer and will without a doubt exceed your expectations. Because when we have the sun, the beach, and the Caribbean Sea, we are happy 😉