After spending more than a year at home, we’ve been dreaming of a Caribbean vacation. Dave and I have been lucky to visit a lot of the Caribbean Islands and to help inspire a trip south this winter, we thought we’d share the most beautiful Islands in the Caribbean to spark your wanderlust.
Beautiful Caribbean Islands to Visit This Winter
The Caribbean is our winter playground. Canadians love to jet off to the islands to enjoy white sand beaches, swaying palm trees, and balmy weather. To ignite the dreamer in you, we’re rounding up the most beautiful Caribbean Islands. Let’s get right into it, shall we?
1. St. Lucia
St. Lucia is arguably the most beautiful of all Caribbean Islands with its two UNESCO World Heritage designated Pitons standing proud. The Gros and Petit Pitons are two mountainous volcanic plugs that definitely contribute to the island’s beauty. With white sandy beaches, dense jungles, and private villas dotting the coast, this is our number one choice for travel to the Caribbean for honeymooners and couples.
When looking for a private villa in St. Lucia check out these two magnificent resorts that we stayed at. Calabash Cove is a luxury boutique all-inclusive resort and spa that caters to adults only. We loved our stay here and it had everything we could hope for in a romantic vacation. Stonefield Villas Resort has incredible views of the Petit Piton. It is locally owned and operated and was one of the first resorts opened near Soufriere.
There is no doubt that Jamaica is our favorite Caribbean Island. As much as we wanted to put it at the top of the most beautiful Caribbean Islands, it comes a close second.
The beaches of Jamaica though, are second to none with the incredible 7-mile Beach in Negril to the secluded Treasure Beach in the South and the famous beaches of Montego Bay. Jamaica has it all – dense jungles, rocky sea cliffs, tiered waterfalls, and white sand. Read: 33 of the Best Things to do in Jamaica
Where to Stay in Jamaica
We have stayed all over the island of Jamaica. These are a few of our favorite resorts in Jamaica. Also check out these: Jamaica Travel Tips
- Hyatt Zilara Rose Hall – Montego Bay – is in a great central location. It also had a lot of activities including SUP, kayaking and sailing included in the booking. Watch our video tour of the Hyatt Zilara. Check out Availability & Prices on Trip Advisor
- Hotel Riu – Montego Bay – Riu Hotel Montego Bay offers a freshwater swimming pool, Jacuzzi, sauna, gym, and wellness center. Check out Availability & Prices on Trip Advisor
- Half Moon – Montego Bay – This 400-acre resort has 2 miles of private white sand beach. It has 3 restaurants and 5 bars. Check out Availability & Prices on Trip Advisor / Booking.com
- Stay at Jakes Resort – St. Elizabeth – We suggest staying at Jakes’ Resort in St. Elizabeth. Located in the south end of the island and feels like you are in the true Jamaica. Read more: Best All Inclusive Hotels in Jamaica
3. Exuma Cays Bahamas
When flying over the Exumas from Nassau in the Bahamas, our jaws dropped as the beautiful scene transpired below. The Exuma Cays of the Bahamas consists of 365 islands and atolls dotting gin blue waters. Spanning 176 miles of crystal clear waters. While technically in the Atlantic, The Exumas are often lumped in with the Caribbean Islands and we couldn’t do this list without including our favorite island paradise.
The Exumas have some of the best animal encounters in the Caribbean where you can swim with sharks, meet the resident pigs, and at Major Cay and snorkel in the surreal Thunderball Grotto that feels like its own colorful fishbowl. If you are looking for a great place to stay, check out Embrace Resorts on Staniel Cay. It is locally owned and operated and is a wonderful couple’s escape in the heart of the Exumas.
4. Cayman Islands
The Cayman Islands are one of the best places in the Caribbean Islands to go scuba diving. They are also one of the most beautiful Caribbean Islands that we’ve seen. With its own Seven Mile Beach, we could walk for days on its white sand leading out to crystal clear turquoise waters.
The Cayman Islands are famous for their clear waters. The deep drop wall dives, Cayman Trench allow for deep diving in crystal clear water and endless visibility. We stayed in the Ritz Grand Cayman on Seven Mile Beach and it was heavenly. If there is one place to splurge on a Caribbean vacation, it is at the Cayman Islands.
One of our favorite Caribbean destinations is Mexico, and the Island of Cozumel is located just off the coast in the Caribbean Sea. Cozumel is famous for its scuba diving and nowhere compares to diving here on Palancar Reef.
It’s the second-largest coral reef in the world! With turquoise water, and powdery white sand world-class diving, it should be at the top of your Mexican vacation. One of the best things to do is to head to another paradise island, Isla Ballestas to swim in its clear blue waters and to book a tour to see whale sharks migrating through. Read more: Swimming with Whale Sharks Cancun – A Massive Adventure
Havana is arguably the most beautiful city in the Caribbean. This UNESCO World Heritage Site is filled with classic cars lining the streets of pastel buildings. With idyllic beaches, historic cities, and lush forests, it has long been at the top of many a Canadian vacation destination.
While Cuba has had its share of difficulties, it is a beautiful island to visit and the people are the friendliest in the Caribbean. Book a stay at a Casa Particular, rent a motorcycle and travel the island independently and you’ll fall in love with Cuba.
We had the opportunity to visit the beautiful island of Curacao on a Caribbean cruise. Its colorful waterfront completely blew us away. Part of the ABC Islands (including Aruba and Bonaire) Curaçao is a Dutch colony in the Lesser Antilles. It is known as the Amsterdam of the Caribbean, and for good reason.
The colonial architecture lines the waterfront and Curacao also houses beautiful beaches and quiet coves. The trade winds keep this Caribbean island a pleasant temperature year-round and is located outside the hurricane belt, there is not a bad time to visit Curacao. Read more: Best Caribbean Islands for Watersports
8. St. Kitts
St. Kitts was an island that we had never heard of before visiting. Once we did, we knew that this was a shining star of the Caribbean Islands. Hiking to the top of the volcano Mt. Liamuiga offers views of the thick rainforest that dominates the mountainous island. Or take a zipline adventure to see the green jungle from above.
With waterfalls, long sandy beaches, and a cloud forest St. Kitts is definitely an island to put on your Caribbean Bucket List. But what is the best thing to do in St. Kitts? Limin’ of course. (it’s the endearing term to relax.) And here’s a fun fact, this island has monkeys!
Located right next door to St. Kitts, Nevis is a volcanic island that is considered a twin island to St. Kitts. With golden sand beaches, old plantations, and old-fashioned rustic charm, the Caribbean Island of Nevis is quickly growing to the top of many people’s favorite Caribbean islands.
The crystal clear waters are perfect for snorkeling and like St. Kitts, it too has a population of African Green Vervet Monkeys. Check out 13 Unique Beaches To Visit in Your Lifetime
Aruba is another one of the ABC Islands of the Caribbean. Aruba, Bonaire, and Curacao are the three westernmost islands of the Leeward Antilles in the South Caribbean. Like Curacao, it is located outside the hurricane belt, has the lovely trade winds to keep temperatures constant, and houses the classic white sand beaches and turquoise waters of the Caribbean islands. There are also some pretty cool landscapes to explore.
Aruba is known for its powdery soft sand beaches and since all beaches in Aruba are public, you are free to go beach hopping to explore the beauty for yourself. And like Curacao, Aruba has pastel Dutch colonial architecture that is great for strolling through pretty streets while shopping. Read next: Best Unique Cruises on Seven Continents
11. Dominican Republic
Dave and I took our honeymoon in the Dominican Republic and it has always had an affection for this beautiful island. The beaches of the Dominican Republic are postcard-perfect with luxury resorts lining the coasts of Punta Cana, Puerto Plata, and La Romana.
The mountainous interior makes it an adventure traveler’s dream, while the colonial architecture of Santo Domingo will attract history buffs. Canadians love traveling to the Dominican Republic. Read more: What My Kids Learned from Living in the Dominican Republic
12. Puerto Rico
Puerto Rico is a great Caribbean Island to visit because Americans don’t even need a passport. This tropical paradise has waterfalls and rainforests, beaches, and a gorgeous heritage center. Puerto Rico may be a part of America, but it feels very much like an international destination.
It is made up of Spanish, African, and Taino (one of the largest indigenous people of the Caribbean Islands) With festivals, outdoor markets, lively nightlife, and unique cuisine (oh, and let’s not forget Rum, lots of rum) Puerto Rico should be put at the top of your Caribbean travel list right now. Read More: 11 Reasons to Visit Puerto Rico This Year
13. Utila, Honduras
Utila is located off the coast of Honduras and was the island where we took our divemasters course many years ago. Utila is certainly one of the most beautiful places to visit in Honduras with secluded beaches and great cheap diving. We swam with whale sharks and explored its extensive underwater world while enjoying seafood on the beach or lazing on a hammock while watching the sunset. Check out Honduras Travel Guide
14. Caye Caulker, Belize
Caye Caulker is an incredible laid-back island in Belize. We chilled on Cay Caulker marveling at the beautiful sandy island. The neighboring island of Ambergris Caye may be more popular, but we loved the laid-back vibe of Caye Caulker. It has some of the best Snorkeling and diving in the Caribbean with Shark Ray Alley located just off its coast.
What we loved the most about Caye Caulker is that there are no cars on the island and we walked through the sandy streets chillaxing on this island paradise. Read more: 16 Amazing Things to Do in Belize One of the coolest things we did in Belize was staying at Deb and Dave’s Resort. Yes, we found a couple with our name! they were so nice, they let us store our dive gear there while we traveled around for a couple of weeks!
15. Turks and Caicos
Turks and Caicos consist of 30 islands and cays and boy are they beautiful! Only 8 are inhabited with Providenciales being the main tourist hub. Take in the history of Grand Turk and Salt Cay and head to Middle Caicos to explore the biggest cave network in the Caribbean Islands.
Have you guessed that Turks and Caicos are surrounded by turquoise waters and sandy beaches? Yes, this is a theme of all Caribbean Islands, and that is what makes the Caribbean such an incredible vacation destination. Grand Turk is one of the best diving destinations in the Caribbean with a wall just a short boat ride offshore. The beaches of Turks and Caicos were created by coral breaks creating beaches of white sands, pink sands, and peach hues.
Barbados is probably at the top of most people’s Caribbean island dream list. It is the most easterly of all Caribbean Islands. In fact, Barbados isn’t technically even in the Caribbean, it’s located entirely in the Atlantic Ocean. Located in the Lesser Antilles, Barbados has soft sand lining the turquoise waters.
With a tropical garden, underground caves, and a British heritage there is something for everyone in Barbados. Plus, Barbados is one of the few Caribbean islands that has monkeys! The others are St Kitts, Nevis, Saint Martin, and Barbados.
We haven’t had the chance to visit Grenada ourselves, but our friend Parm has extensively traveled around and written about it for us. Grenada isn’t as well-traveled as other Caribbean Islands, so be the first of your friends to check it out. With white sandy beaches, colonial cities, plantations, chocolate, and clear waters, there are so many things to do in Grenada you’ll never want to leave. Read more: 20 of the Best Things to do in Grenada
Book this highly rated Barbados Island tour – where you’ll drive through the natural beauty of the Scotland District of Barbados, stop at St. John’s Paris for panoramic views, and the capital city of Bridgetown, to explore the rich history of Barbados at Bridgetown’s Garrison, a UNESCO World Heritage Site.
18. St. Maarten
Speaking of Saint Martin, Sint Maarten is made up of two territories. One French and one dutch. St. Maarten is the Caribbean Island that is famous for airplanes landing extremely close to beachgoers. It’s known as the culinary capital of the Caribbean there are also a lot of adventures to be had.
From the world’s steepest zip line to climbing Pic du Paradis Mountain there is a lot more to do than just relaxing on its pristine beaches. When visiting St. Maarten you can also go Caribbean island hopping on day trips to nearby Aguilla, Saba, or St. Barths.
19. U.S. Virgin Islands
I am so jealous that the United States has its own tropical islands. Canada was once trying to get a tropical island where we could easily escape our winters, but the country wouldn’t let Prime Minister Pierre Trudeau purchase it. So alas, we look on with envy to our neighbors to the south.
The US Virgin Islands consist of St. Croix, St. John, and St. Thomas and they are known to have some of the world’s most stunning beaches, with crystal clear waters and soft white sand. The islands are surrounded by lush green hills and mountains, offering a beautiful contrast to the turquoise waters of the Caribbean Sea.
This island is so appealing to Americans because you do not need a passport to visit it if you are an American citizen. Lucky you!
20. British Virgin Islands
The British Virgin Islands have some of the most beautiful beaches in the Caribbean. White sand, turquoise waters, and lush greenery make for a stunning natural setting. They are known for their excellent sailing and boating opportunities. The calm waters and steady trade winds make for ideal conditions, and there are many marinas and yacht clubs to cater to boaters.
With over 60 islands and cays, which makes island hopping is a popular activity. Each island has its own character and charm, from the quiet and secluded Jost Van Dyke to the lively and cosmopolitan Tortola.
It is also committed to eco-tourism, with a focus on sustainable development and preserving the natural environment. Visitors can participate in activities such as hiking, birdwatching, and visiting nature reserves and national parks.
There are so many more Caribbean Islands to visit. It’s impossible to round them all up in one post. While we haven’t been to all of them yet, we look forward to exploring more and adding them to our list as we check off more great Caribbean Islands to visit.
Part of the fun of travel is getting to go places you haven’t been to yet. What Caribbean Island should we visit next?
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