Find the Best Caribbean Islands for Every Month of the Year

January: Warmth in the Virgin Islands

January travelers often seek warmth, and the Virgin Islands — both U.S. and British — typically offer some of the most pleasant temperatures in the Caribbean. From the colonial charm of Christiansted on St. Croix to the rugged terrain of Virgin Gorda, there’s a wide range of experiences. U.S. citizens visiting the U.S. Virgin Islands generally do not need a passport, making travel even easier.

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

February: Sunshine and Celebration in Trinidad

February is known for sunny skies across the Caribbean, and Trinidad is among the sunniest destinations. It’s also home to one of the region’s most vibrant Carnival celebrations, typically culminates on the Monday and Tuesday before Ash Wednesday. Beyond the festivities, Trinidad is known for its lush waterfalls and scenic landscapes.

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

March: Spring Break in Jamaica

Jamaica is a popular destination for spring travelers, including students, educators, and families. Negril Beach offers stunning views, warm breezes, and a relaxing atmosphere. Accommodations range from private villas to boutique resorts like The Caves or the stylish Rockhouse.

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

April: Diving Adventures in the Cayman Islands

The Cayman Islands are renowned for world-class diving. Sites like the USS Kittiwake wreck, Bloody Bay Marine Park, and the Grand Cayman Wall offer diverse underwater experiences. Dive shops and instructors are widely available, making it accessible for both beginners and seasoned divers.

May: Exploration in St. Lucia

May is ideal for outdoor exploration, and St. Lucia’s dramatic Pitons — twin volcanic peaks — offer unforgettable hiking opportunities. Trails, boat tours, and rainforest excursions (like En Bas Saut) provide multiple ways to experience the island’s natural beauty.

June: Sailing in the Grenadines

June’s breezes make the Grenadines perfect for sailing. Islands like Bequia and Mustique are best explored by boat, and local resorts can help arrange charters or excursions tailored to your interests.

July: Hiking in Puerto Rico

Puerto Rico offers rewarding hikes with scenic views. While El Yunque National Forest continues to recover from past hurricanes, trails like Mt. Britton provide a short but challenging hike with panoramic views from the summit tower.

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

August: Beach Time in Aruba

August is a great time to enjoy Aruba’s beaches. Eagle Beach features soft white sand and clear waters, and visitors may even spot nesting sea turtles at night. Andicuri Beach offers windsurfing, snorkeling, and bodyboarding for active beachgoers.

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

September: Culinary Delights in Turks and Caicos

Turks and Caicos is known for its conch dishes — a Caribbean staple. Start at Da Conch Shack near Grace Bay Beach, then explore Bugaloos Conch Crawl in Five Cays. For upscale dining, Stelle Restaurant at Gansevoort offers refined seafood options in a tropical setting.

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

October: Storm-Safe Travel in Curacao

October marks the height of hurricane season in the Caribbean. Southern islands like Curaçao are less frequently impacted, though travel disruptions may still occur. Curaçao’s Dutch heritage is reflected in its architecture, especially in the capital city of Willemstad. Inland, Christoffel National Park offers hiking and wildlife viewing, including sunrise safaris.

Tip: Consider a travel protection plan when traveling during hurricane season*. Plans may include benefits for Trip Cancellation, Trip Interruption, and Emergency Assistance & Transportation.

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

November: Ecotourism in Dominica

Dominica, often called the “Nature Island,” is one of the Caribbean’s most biodiverse destinations. Morne Trois Pitons National Park is home to the rare Sisserou parrot, and the island’s black-sand beaches, waterfalls, and cliffs offer stunning scenery. Dominica is also known for frequent whale sightings, especially sperm whales.

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

December: Peace and Quiet in Anguilla

December travelers often seek tranquility, and Anguilla delivers. Resorts like Zemi Beach House and Cap Juluca offer serene escapes. The island’s slower pace and uncrowded beaches make it a perfect place to unwind during the holiday season.