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Which Caribbean Islands Should You Visit? (Updated for 2022)

When you truly need to get away from it all, there's nothing quite like one of the many Caribbean Islands - here are the best of the best.

Many restless travelers flock to the beautiful Caribbean islands when they need to get away from it all. It is safe to say that the Caribbean is abundant with places that will take you on a whirlwind journey across palm-fringed coastlines, culturally rich communities, and blue waters that seem to shimmer for miles.

The Caribbean is one of the most enchanting vacation destinations in the world. With over 7,000 islands and 13 separate nations, the region boasts countless tropical island settings, making it one of the most visited holiday destinations globally.

Where should you plan your next vacation though?

What Are the Prettiest Caribbean Islands

Cayman Islands

The Cayman Islands — Grand Cayman, Cayman Brac, and Little Cayman — have some of the best stretches of coastline in the entire Caribbean. . . Did someone say beachside cocktail? Proudly known as the culinary capital of the Caribbean, visitors can delight in fresh plates of seafood and farm-to-table produce. At the same time, those looking for exciting nightlife can dance the night away in the salty ocean air. The underwater activities are just as thrilling since the Cayman Islands are popular among scuba diving enthusiasts.

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Who hasn’t dreamed of hot nights in Havana? Old Havana’s streets are perfect for strolls and taking in the historic buildings. Head 180km west for something greener – to the island’s Viñales Valley, situated in the inland province of Pinar del Río. Easily one of the most beautiful places in the entire country. The dome-like limestone mountains and lush scenery have earned the region UNESCO World Heritage status. From Havana’s bright architecture to the beautiful Varadero beach, to the pine-scented Viñales – Cuba’s prettiness knows no bounds.

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St. Lucia

St Lucia is one of the prettiest islands for apparent reasons. The picturesque destination is ideal for travelers seeking an escape from the ordinary. The skyscraping Piton mountains have earned more than a few jaw-dropping reactions. The volcanic peaks – Gros Piton and Petit Piton – are the island’s most iconic landmarks, and tourists can experience their dramatic effect with either a guided hiking tour to the top or from a beach towel on Sugar Beach. Volcanic beaches, hot-springs, and striking scenery – St. Lucia naturally meets many vacation dreams.

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Which Are the Safest Caribbean Islands?


Known as the most colorful capital of the Caribbean – Curacao’s capital city Willemstad is decorated with traditional bright pastel-colored buildings and Dutch-inspired architecture. Located below the hurricane belt with a low crime rate, Curacao is the best Caribbean island to visit for off-the-beaten-track explorations. A medium-sized island that is also incredibly diverse. Locals speak multiple languages, including English, Dutch, Spanish, and Papiamentu. This Caribbean island’s focus goes beyond tourism, offering guests a more private island holiday experience and the chance to live like a local.

Which Caribbean Islands Should You Visit in 2021?
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The British Virgin Islands

One of the largest island chains and most visited, The British Virgin Islands are a very safe destination for travelers. Offering the best of both worlds since the island boasts the beautiful merging of the Caribbean Sea and the North Atlantic Ocean. Perhaps the most unique travel spot in the chain is the Virgin Gorda, or The Baths – every adrenaline junkie’s delight with massive granite boulders and crystal-like waters. In fact, the British Virgin Islands is the best Caribbean island to visit for water sport enthusiasts! The adventures never stop here.

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Nicknamed the Emerald Isle of the Caribbean for both the terrain and the cultural heritage. Montserrat is considered one of the safest Caribbean islands – with its most significant threat being the active Soufrière Hills volcano and hurricanes season between June and November. A charming little island that shares the stretch of the Caribbean Sea, Montserrat’s enjoys popularity from its star attraction: the Soufriere Hills Volcano. The newly-built capital island Brades boasts a rainforest lush with exotic flora and fauna, while the deserted old capital city, Plymouth, is ideal for an off-the-grid adventure.

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Which Caribbean Islands Are the Most Luxurious?

St. Barts

A truly one-of-a-kind island. If you want a grandeur Caribbean experience, then St. Barts is the island for you.  St. Barts is a Caribbean Island frequented by the rich and famous. Despite its small size, tourists can enjoy lavish activities such as luxury yachts tours around the glistening waters, shop at exclusive designer stores, and watch cactus plants bloom at night. The culture of St. Barts is distinct from the other islands and offers sophisticated local bistro dining, laidback nightlight experiences, and some of the most luxurious resorts on the planet.

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Martinique is the literal smorgasbord of the Caribbean Islands. The stunning rugged terrain offers some of the best hiking in the Caribbean region. On the other hand, the island’s quiet sophistication allows for slow days spent meandering through narrow streets, taking in the architectural sites, such as Schoelcher Library and St. Louis Cathedral. Foodies can also delight in some of the best Creole food in the Caribbean, while the Dillon distillery offers a peek (and a taste) into the island’s vintage rum production. Centerpiece beaches, culinary experiences, and historical charm, Martinique is ripe with luxury.

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Turks and Caicos

Consisting of little islands with nearly deserted beaches and waters of different shades of blue, the Turks and Caicos are oozing with luxury. Home to world-famous restaurants, hotels, and spas, the island chain offers water sports in sparsely populated areas and complete serenity. This Caribbean island region is perfect for those seeking mellow retreats on fine white sand. Boasting some of the world’s most incredible coral reefs and coastlines, Turks and Caicos have built themselves into true luxury-tourism destinations.

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Tips for Traveling to the Caribbean

  1. Don’t Assume All Islands Are the Same. It’s tempting to group the Caribbean into one destination – but in reality, no two islands are alike. Your experience on St. Lucia will be vastly different from what you’ll encounter in the Dominican Republic, and the archipelagos like the Bahamas, Nassau is a world away from the Out Islands.
  2. Don’t Expect All-inclusive Hotels. You may have booked an island vacation, but that certainly doesn’t mean everything is included in the price upon arrival. There are all-inclusive options across the Caribbean, but it’s usually an expensive mistake to assume all accommodations in the region cover room, board, activities, and more.
  3. Explore Beyond the Hotel Grounds. It may be appealing to stay close to your property, but you’d be doing yourself and the region a disservice if you didn’t venture off hotel grounds to do some exploring.
  4. Don’t Be Afraid to Visit in the Off-Season. Avoiding peak travel times and holidays will mean better deals, fewer crowds, and a vacation catered to your needs. Besides, the weather in the Caribbean is usually warm and pleasant all year round.
  5. Take Hurricane Season Into Account. Peak hurricane conditions occur from mid-August through late October. Hurricanes are common in the Caribbean region, but they’re not guaranteed, and many are minor or fizzle out before making landfall. A local secret: some Caribbean islands are located entirely outside of the Hurricane Belt – so places like Barbados, Saint Vincent and the Grenadines, Trinidad, and Tobago, and Grenada are seldom at risk of a storm.
  6. Island-Hop (With Or Without A Cruise). Cruising the Caribbean is a great way to visit the region, but it’s not the only option. If you want to see multiple islands and be in charge of your schedule, then hop between islands via ferry or a short flight.
  7. Plan Water Activities. The Caribbean island’s warm, crystal-clear waters is a major draw card. Make sure you take full advantage of this pristine, inviting opportunity by learning to snorkel or dive before your trip.
  8. Don’t Assume Everyone Speaks English. Although many Caribbean islands will feel familiar, English isn’t the first language spoken on all – and each island has a culture that beats to its own drum. You’ll also find a large concentration of Dutch, French, and Spanish.
  9. Cell Signal isn’t Guaranteed. Although most of the Caribbean is populated and modernized, they’re still islands. Strong cell signal isn’t a given, and Wi-Fi can be a hit or miss.
  10. Not All Local Water Is Safe For Consumption. While most of the Caribbean has water safe to drink directly from the tap (especially inside resorts), not all areas do. So be safe by checking before filling bottles straight from the faucet.
  11. Look Up Prices Beforehand. If you head to the Caribbean expecting low prices, you might be shocked at the numbers on menus and services across the region. Prices are higher, not lower, on islands. Their total isolation from other parts of the world, means that most supplies, tools, and ingredients are imported, and you’ll see that tax reflected on the final value of goods and services you’re purchasing. So, budget accordingly.
  12. Carry Cash With You. As with anywhere, you’ll want to carry cash on your trip to the Caribbean. Many islands accept the US dollar but do a little investigating to determine if your destination warrants securing some local currency too. .
  13. Buying Souvenirs. Try to find a market where you can support local artists and makers. You (and your loved ones) will get a lot more value from souvenirs like homemade Jamaican jerk seasoning, Bahamian straw bags, and Barbados rum than you would from a generic T-shirt or key chain.

Are you daydreaming of sunbathing under waving palms with a coconut drink in hand? How about exploring miles of unspoiled coastlines with fine white sand and crystal-clear waters? The Caribbean islands are practically synonymous with the word vacation. So, whether you’re searching for something more refined or something a little rough around the edges, you’re sure to enjoy your dream tropical island holiday somewhere in the Caribbean.


Jenny Cohen Drefler

Jenny Cohen Derfler

Air Dr CEO & Co-Founder

Jenny is the CEO and one of the Co-Founders at Air Doctor. She spent more than 20 years at Intel, most recently as general manager of its manufacturing facility in Israel and before that in various engineering and manufacturing roles in Silicon Valley. Air Doctor is her second startup having previously founded electric vehicle company ElectRoad.