Find the Best Caribbean Islands for Every Month of the Year

The beauty of the Caribbean is that no two islands offer the same experience, and every traveler will find something different and special about each island.

With that in mind, we chose our best Caribbean islands for every month of the year. Obviously, your choices might differ – but that’s the beauty of the region – so many awe-inspiring destinations. That and the white-sand beaches and swaying palms and delightful breezes and … oh, just read on.

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The Best Caribbean Islands for...

January: Warmth in the Virgin Islands

Most visitors to the Caribbean in January want warmth, period. Every island is likely to be warmer than back home, but some of the warmest Caribbean destinations are the Virgin Islands, U.S. and British.

Not only are the Virgin Islands warm, but they offer a plethora of experiences, from the gorgeous colonial vistas of Christiansted, on St. Croix, to the wild and rugged inland of Virgin Gorda. And the best part about visiting the U.S. islands is you don’t even need a passport!


Also read: The Best Cities to Visit in The World for Each Month of the Year

February: Sun in Trinidad

February cries out for sun. You’re pretty much guaranteed sun in the Caribbean in February, but one of the sunniest destinations is Trinidad – and the good news is that you can catch Trinidad’s spectacular Carnival and Mardi Gras celebration all month.

Mardi Gras not your thing? Trinidad is known as the island of waterfalls. Not a bad consolation prize.


Also read: 8 of the Best Spring Vacation Ideas Around the World

March: Party in Jamaica

Spring Break? Jamaica? Yah mon.

Here’s a secret: More schoolteachers than students visit Jamaica over Spring Break. And the resorts around Negril Beach are uncrowded, with everything you go to the Caribbean for – spectacular beaches, warm breezes, and the feeling that the real world is a million miles away.

Lodging options are many, from villa rentals to high-end accommodations like The Caves, with the Rockhouse a more-than-reasonable compromise.

Also read: Alternative Spring Break Destinations to Get Away from the Crowds

April: Diving in the Caymans

The Caymans are synonymous with great Caribbean diving, with as many as five of the world’s top 10 dive sites.

And talk about variety: You can explore sunken ships like the USS Kittiwake, see a breathtaking array of marine life at Bloody Bay Marine Park, or explore the north side of the Grand Cayman Wall, most notably the depths of Babylon.

Vacation and gear rentals are plentiful, and lessons are available. So jump in!

May: Exploring in St. Lucia

May is a month for exploration – and one of the best islands for exploring is St. Lucia.

You’ll understand why with your first glimpse of the pitons, the twin volcanic peaks that burst out of the tropical landscape, promising a hike that’s not for the timid or out-of-shape.

St. Lucia in the Caribbean
Vacation under a rainbow in St. Lucia

Trails wind up both pitons, boat tours give you the ocean view, and many local hotels are situated to give you max piton out your window.

For a change of pace, explore the island’s rainforests, especially the En Bas Saut.

June: Sailing in the Grenadines

In June a nice breeze is just the thing – and that means sailing in the Grenadines.

These small islands, which include Bequia and Mustique, are built for sailing, in part because that’s the best way to get from island to island.

Ship rentals and excursions are everywhere in the Grenadines. Any hotel or resort on the islands can steer you to the right operator and experience for you.


July: Hiking in Puerto Rico

If you’re up for some hiking this month, Puerto Rico is a hiker’s paradise, with great scenery and ample rewards at the end of the trail.

The La Mina Trail in El Yunque National Forest is the quintessential Puerto Rican hike, but it’s still in hurricane-recovery mode; in the meantime, the Mt. Britton Trail offers a short-but-challenging hike and amazing views from the stone recreation tower at trail’s end.

Also read: 6 Best Hiking Trips in the U.S. and How to Find Trails Near You

August: Beaching in Aruba

In August, you may be feeling like getting your last beach fix before hunkering down.

Aruba is the place to go, and two beaches in particular: Eagle Beach, with its soft white sands and clear-blue water, where you can see turtles laying eggs in the sand at night; and Andicuri Beach, with its windsurfing, swimming, bodyboarding, and snorkeling.

Also read: Best Caribbean Beach Resorts -- Jamaica, Bahamas, Turks and Caicos and Beyond

September: Eating in the Turks and Caicos

Conch, one of the Caribbean’s quintessential seafood dishes, is the Turks and Caicos’ specialty. You can get conch any way you like here, from chowder or fritters at a beachside shack to more adventurous treatments at a world-class resort restaurant.

Start at the aptly named Da Conch Shack on beautiful Grace Bay Beach, then move on to Bugaloos Conch Crawl in Five Cays, where you can sample an array of conch entrees (Buffalo conch!) in a gorgeous tropical setting. For more upscale dishes, try Stelle Restaurant at Gansevoort Turks + Caicos.

Also read: Best Restaurants in the Caribbean -- Find Island Flavors on Your Next Trip

October: Avoiding the storms in Curacao

Unfortunately, October is the start of the Caribbean hurricane season; however, hurricanes are not as prevalent in the southern and western islands – like Curacao. That said, travel insurance is especially important when traveling in the Caribbean during hurricane season, as you may encounter disruptions.

The Dutch feel remains strong, creating an interesting culture and some gorgeous architecture, especially in the capital, the World Heritage Site of Willemstad.

Once you head inland, Christoffel National Park has hiking trails and vehicle tours, with sunrise safaris where you can catch some of the island’s endangered species.

Also read: 
• Weathering the Storm—Preparing for Travel During Hurricane Season
• Hurricane Travel Insurance: What You Need To Know

November: Ecotourism in Dominica

The Caribbean’s “Nature Island,” Dominica is one of the most biodiverse locations in the Caribbean, with hundreds of native rare or endangered species.

Catch the native Sisserou parrot at Morne Trois Pitons National Park — and even if you miss the parrot, the black-sand beaches, steep cliffs and incredible waterfalls will more than make up for it.

And did we mention that Dominica is the whale-watching capital of the Caribbean?

Also read: 10 Eco-Friendly Travel Tips to Reduce Your Carbon Footprint


December: Getting away from it all in Anguilla

Come the holidays, you want to escape the crowds. Some of our favorite getaways are on Anguilla, from simple rentals to upscale resorts like the Zemi Beach House or the old favorite Cap Juluca.

Anguilla doesn’t overflow with things to do, but that’s the point. It’s a place to get away and unwind in a manner only the Caribbean can provide.

Travel Insurance for the Caribbean

No matter when you travel to the islands of your dreams, consider getting travel insurance from a reputable company like Generali Global Assistance. Whether you’re worried about having to cancel your vacation, medical emergencies on your trip, lost bags or a stolen passport, our plans can help you rest easier while relaxing on your white sandy beach in the sun.

Also read: Top 5 Reasons to Get Travel Insurance

We’d love to know what you think are the best Caribbean islands for every month of the year. Share with us at FacebookTwitter and Instagram!


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