Top 20 Must-Visit Caribbean Islands for Your Travel Bucket List

After spending more than a year at home, we’ve been dreaming of a Caribbean vacation. Dave and I have been fortunate to explore many Caribbean Islands, and to inspire your travel plans for this winter, we’re excited to share information about the most beautiful islands in the Caribbean that are sure to ignite your wanderlust.

Beautiful Caribbean Islands to Visit This Winter

The Caribbean serves as our winter playground. Many Canadians adore jetting off to the islands for white sandy beaches, swaying palm trees, and warm weather. To inspire your journey, we’ve curated a list of stunning Caribbean Islands. Let’s dive into our selections!

1. St. Lucia

St. Lucia is considered one of the most beautiful Caribbean Islands, highlighted by its two UNESCO World Heritage-designated Pitons. The iconic Gros and Petit Pitons are magnificent volcanic plugs that enhance the island’s splendor. Featuring white sandy beaches, lush jungles, and private villas, this destination is perfect for honeymooners and couples.

We recommend exploring two exquisite resorts in St. Lucia. Calabash Cove is a luxury boutique all-inclusive resort and spa that caters exclusively to adults. Our stay here was unforgettable, offering everything we desired in a romantic getaway. Stonefield Villas Resort presents incredible views of the Petit Piton and is locally owned, providing a unique experience near Soufriere.

2. Jamaica

Jamaica ranks as our favorite Caribbean Island. While we would love to place it at the top of the list, it holds a close second overall.

Jamaica’s breathtaking beaches are unparalleled, from the stunning 7-mile Beach in Negril to the more secluded Treasure Beach in the South, along with the vibrant beaches of Montego Bay. Jamaica boasts rich jungles, rocky cliffs, tiered waterfalls, and vibrant white sands.

Where to Stay in Jamaica

Our travels across Jamaica have led us to various delightful resorts. Here are a few favorites:

• Hyatt Zilara Rose Hall – Montego Bay offers a prime location and activities like SUP, kayaking, and sailing included in the stay.
• Hotel Riu – Montego Bay – Features a freshwater swimming pool, Jacuzzi, sauna, gym, and wellness center.
• Half Moon – Montego Bay – A sprawling 400-acre resort with 2 miles of private beach.
• Jakes Resort – St. Elizabeth – A memorable stay in the serene south end of the island, offering a true Jamaican experience.

3. Exuma Cays Bahamas

Viewing the Exumas from above when flying from Nassau was breathtaking. The Exuma Cays, with their 365 islands and atolls, are surrounded by stunning blue waters, covering 176 miles of crystal-clear coastline. Although located in the Atlantic, these islands are often grouped within the Caribbean category and certainly deserve mention.

The Exumas provide fantastic animal encounters, including opportunities to swim with sharks, meet the iconic pigs at Major Cay, and snorkel in the mesmerizing Thunderball Grotto, a vibrant underwater haven. For accommodations, consider the locally-owned Embrace Resorts on Staniel Cay, perfect for a romantic escape in the heart of the Exumas.

4. Cayman Islands

The Cayman Islands are renowned for some of the best scuba diving in the Caribbean, showcasing incredible natural beauty. With their famed Seven Mile Beach, visitors can walk for miles along pristine white sands that extend into sparkling turquoise waters.

The islands are recognized for their crystal-clear waters and remarkable diving opportunities, particularly at the Cayman Trench, which offers impressive visibility. Our stay at the Ritz Grand Cayman, located right on Seven Mile Beach, was paradise.

5. Cozumel

Cozumel, one of our favorite Caribbean destinations, is located just off the coast of Mexico. This island is famed for its exceptional scuba diving, particularly at Palancar Reef.

As the world’s second-largest coral reef, Cozumel boasts turquoise waters and powder-soft sand, providing an unparalleled diving experience that should be incorporated into any trip to Mexico.

6. Cuba

Havana often stands out as the most beautiful city in the Caribbean. This UNESCO World Heritage site is filled with classic cars set against pastel buildings, combining idyllic beaches, historical charm, and lush jungles.

Cuba may face challenges, yet it remains a captivating destination, thanks to the friendliness of its people. Experiencing a stay at a Casa Particular, renting a motorcycle, and exploring the island offer a great way to fall in love with this Caribbean gem.

7. Curacao

Our visit to Curacao during a Caribbean cruise was unforgettable. The island’s colorful waterfront and charming Dutch colonial architecture are simply enchanting. As one of the ABC Islands (including Aruba and Bonaire), Curacao offers marvelous beaches and tranquil coves.

Thanks to the trade winds, Curacao enjoys pleasant temperatures year-round, making it an ideal destination outside of the hurricane belt.

8. St. Kitts

St. Kitts was a rather unexpected discovery. Upon exploring, we realized it truly shines among Caribbean Islands. Hiking up Mount Liamuiga rewards visitors with breathtaking views of a lush rainforest, while ziplining reveals the island’s verdant beauty from above.

With picturesque waterfalls, expansive beaches, and a captivating cloud forest, St. Kitts is an absolute must for your Caribbean bucket list. And don’t forget to enjoy some “limin’,” a local term for relaxation.

9. Nevis

Neighboring St. Kitts, Nevis is a volcanic island with golden sand beaches, historic plantations, and rustic charm that is quickly gaining popularity among travelers.

The clear waters are perfect for snorkeling, and like St. Kitts, it’s home to a population of African Green Vervet Monkeys.

10. Aruba

Aruba is another captivating member of the ABC Islands in the Caribbean. Aruba, Bonaire, and Curacao make up the westernmost islands of the Leeward Antilles. Aruba enjoys a location outside the hurricane belt and consistently benefits from lovely trade winds.

The island is renowned for its soft sand beaches, and with all beaches being public, the opportunity to beach hop and explore the stunning landscapes is enticing. Aruba’s charming pastel-colored Dutch architecture invites leisurely strolls through its quaint streets.

11. Dominican Republic

The Dominican Republic holds a special place in our hearts, as it was the destination for our honeymoon. The island showcases postcard-perfect beaches lined with luxury resorts in Punta Cana, Puerto Plata, and La Romana.

Adventurous travelers will appreciate the mountainous interior, while history enthusiasts can explore the colonial architecture of Santo Domingo.

12. Puerto Rico

Puerto Rico stands as a fantastic Caribbean Island for travelers, particularly as Americans do not require a passport to visit. This tropical paradise showcases mesmerizing waterfalls, lush rainforests, and rich cultural heritage.

With vibrant festivals, outdoor markets, exciting nightlife, and distinct cuisine featuring a vast array of rum, Puerto Rico should undeniably be at the top of your Caribbean travel agenda.

13. Utila, Honduras

Utila, located off the coast of Honduras, dazzles visitors with secluded beaches and affordable diving experiences. The island is noted for whale shark encounters and rich marine life, making it a perfect getaway for diving enthusiasts.

14. Caye Caulker, Belize

Caye Caulker’s laid-back atmosphere makes it an alluring destination in Belize. Although nearby Ambergris Caye may attract larger crowds, we found Caye Caulker’s serene vibe irresistible.

The island boasts some of the finest snorkeling and diving opportunities in the Caribbean, particularly at Shark Ray Alley, which lies just off the coast.

15. Turks and Caicos

Comprising 30 islands and cays, Turks and Caicos is a breathtaking destination. Of those, only 8 are inhabited, with Providenciales as the main tourist hub. Discover the historical significance of Grand Turk and Salt Cay or venture to Middle Caicos to explore an expansive cave network.

As anticipated, Turks and Caicos is famous for its turquoise waters and pristine beaches, which create an idyllic vacation atmosphere. Grand Turk offers exceptional diving opportunities just a short boat ride away.

16. Barbados

Barbados frequently ranks at the top of many travelers’ Caribbean island wish lists. While technically located in the Atlantic Ocean, it lies within the Lesser Antilles and boasts soft sandy shores along turquoise waters.

The island features a tropical garden, underground caves, and a vibrant British heritage which caters to all types of visitors. Notably, Barbados is also one of the few Caribbean islands that are home to monkeys.

17. Grenada

While we haven’t visited Grenada, our friend Parm has extensively explored and documented his travels for our readers. As one of the lesser-known Caribbean Islands, Grenada promises unique experiences filled with white sandy beaches, colonial towns, chocolate plantations, and exceptionally clear waters.

18. St. Maarten

St. Maarten is a fascinating Caribbean Island split into two territories—French and Dutch. It’s renowned for its close proximity of airplanes landing near sunbathers, offering a striking view for both thrill-seekers and travelers alike.

This culinary capital is packed with adventures ranging from extreme ziplining to navigating stunning mountain trails. On your visit, consider taking day trips to neighboring islands such as Anguilla, Saba, or St. Barths.

19. U.S. Virgin Islands

The U.S. Virgin Islands, comprising St. Croix, St. John, and St. Thomas, dazzle visitors with stunning beaches, crystal-clear waters, and soft white sands. With lush green hills and mountains surrounding the islands, they provide a picturesque backdrop against the Caribbean Sea.

U.S. citizens enjoy an added advantage as they do not require a passport to visit these beautiful islands.

20. British Virgin Islands

The British Virgin Islands are home to some of the Caribbean’s most exquisite beaches. Clear waters, white sandy shores, and verdant landscapes create a magnificent natural setting ideal for relaxation and exploration.

Renowned for excellent sailing and boating conditions, each island offers its unique charm, from the tranquil Jost Van Dyke to the lively Tortola.

Eco-tourism thrives here, encouraging activities such as hiking, birdwatching, and discovering nature reserves while you enjoy the enchanting environment.

There remains a multitude of Caribbean Islands waiting to be discovered, making it nearly impossible to cover them all in one article. Even though we have yet to experience every single one, we look forward to adding those missed treasures to our travel list. The adventure of travel lies in exploring new places; what Caribbean Island should be our next destination?

Plan Your Tropical and Caribbean Vacation With These Resources

• The Most Beautiful Tropical Islands in the World
• 13 Unique Beaches To Visit in Your Lifetime
• 10 Great Things to do in the Caribbean
• 6 Surprisingly Caribbean Water Adventures to do in Northern Michigan
• Best Caribbean Islands for Watersports
• Best Stops on a Florida Keys Road Trip Itinerary
• Discover The Best Beaches in Zanzibar
• 23 Best Beaches in Florida for Fun in the Sun