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Writer's pictureCaptain Nitzan

5 Best Caribbean Destinations to Charter a Boat This Winter

Last week was our yacht club's final Wednesday night race of the season. While sailing in many places in the US may continue through late October / early November, days are getting shorter and sailors are starting to get the winter blues... Hopefully, this article will help, as now is the perfect time to start planning your winter sailing vacation in the Caribbean!

The Caribbean Islands offer some of the best chartering destinations on the planet. Steady winds, tranquil blue waters, secluded bays, or vibrant coastal towns, chartering a boat in a tropical paradise during the winter provides the ultimate getaway. Here are five of the best destinations to charter a boat in the Caribbean this coming winter, offering everything from pristine sailing conditions to diverse marine life and rich cultural experiences.


5 Best Caribbean Destinations to Charter a Boat
The Baths Virgin Gorda, British Virgin Islands

1. British Virgin Islands (BVI)

Why It's Great for Winter Sailing

The British Virgin Islands (BVI) is often referred to as the "Sailing Capital of the World," and for good reason. With more than 60 islands and islets, constant trade winds, and line-of-sight navigation, it's an ideal destination for both novice and experienced sailors. The weather during the winter is warm, with temperatures ranging from 75°F to 85°F, and the winds are steady, typically between 10 to 25 knots, offering perfect sailing conditions.


5 Best Caribbean Destinations to Charter a Boat
Bubbly Pool, Jost Van Dyke, British Virgin Islands

Key Highlights

  • The Baths at Virgin Gorda: One of the most iconic natural wonders in the Caribbean, The Baths feature massive granite boulders, creating hidden pools and grottoes that are perfect for snorkeling and exploring.

  • Jost Van Dyke: Famous for its beach bars and vibrant atmosphere, Jost Van Dyke is home to the famous Soggy Dollar Bar and Foxy’s. It's the perfect place to drop anchor, relax, and soak in the island vibes.

  • Anegada: Unlike the volcanic islands in the BVI, Anegada is a coral atoll known for its flat landscape, beautiful beaches, and abundant marine life. Snorkeling and diving are fantastic here, with coral reefs, shipwrecks, and diverse species to discover.

  • Bubbly Pool: Located on the eastern side of Jost Van Dyke, the Bubbly Pool is a geological delight. This natural Jacuzzi is formed as waves roll through a crevasse in the boulders that line the Northeastern coast of Jost. The waves fill a small pool with effervescent sea water.

5 Best Caribbean Destinations to Charter a Boat
The Soggy Dollar's famous Painkiller cocktail, Jost Van Dyke, British Virgin Islands

Sailing Tips

  • BVI is great for line-of-sight sailing.

  • If you plan to sail to USVI - ensure you're familiar with local customs and navigation.

  • Mooring balls are available in most bays, but it's wise to arrive early to secure a good spot.

  • If you wish to reserve a mooring for the night - use Boaty Ball, where you can make reservations as early as 7am on the day you wish to moore on.



2. St. Martin / Saint Maarten

5 Best Caribbean Destinations to Charter a Boat
Simpson Bay, Saint Maarten

Why It's Great for Winter Sailing

St. Martin/Saint Maarten offers a unique blend of French, Dutch and Creole cultures, stunning beaches, and varied sailing experiences. Winter months see steady winds of around 15 to 25 knots, perfect for both cruising and more challenging open-water sailing. The island serves as an excellent base to explore neighboring islands like Anguilla, St. Barths, and Saba.





Key Highlights

  • Orient Bay: On the French side of the island, this bay is perfect for windsurfing and kite surfing, thanks to its strong, consistent winds. The nearby restaurants offer exquisite French-Caribbean cuisine, ideal after a day at sea.

  • Anse Marcel: A more secluded bay, perfect for those looking to escape the crowds and enjoy tranquil waters. The marina here provides excellent services for charter boats.

  • Grand Case: Located on the northwest side of the Island, this small town is a Caribbean gem! A long strip of cafes, boutiques, shops, and restaurants, serving anything from fine dining to Lolo's - the typical local BBQ. The Grand Case Carnival takes place every Tuesday from 18:00 to 22:00, starting in late January and for 10 consecutive weeks. During carnival nights, AKA Les Mardis de Grand Case, you can enjoy the most diverse and colorful parades as well as a variety of musical performances.

5 Best Caribbean Destinations to Charter a Boat
Mardi Gras Carnival night in Grand Case, St. Martin

Sailing Tips

5 Best Caribbean Destinations to Charter a Boat
Anse Colombier, St. Barths
  • St. Martin has more challenging open-water sailing, so it's ideal for sailors looking to experience a variety of conditions.

  • Be aware of the local maritime regulations, especially when traveling between different territories (French, Dutch and British (Anguilla)).

  • The eastern side of St. Martin is extremely exposed to the Trade Winds, has many shallows near the shore, therefore one should not plan an overnight stay along that coast. The east coast also is impacted by Sargassum, a pelagic brown algae, making the beaches along that coast unpleasant.


5 Best Caribbean Destinations to Charter a Boat
Carriacou, Grenada

3. Grenada and St. Vincent & The Grenadines

Why It's Great for Winter Sailing

Known as the "Spice Island," Grenada is located at the southern end of the Caribbean and offers a mix of untouched natural beauty, vibrant culture, and incredible sailing experiences. The winter season is perfect for sailing, with calm seas and moderate trade winds that make navigation enjoyable. Grenada is also an ideal gateway to explore the Grenadines, including popular spots like Carriacou and Petit St. Vincent.


Key Highlights

  • St. George's: The capital of Grenada, St. George's is one of the prettiest harbors in the Caribbean. Its waterfront is lined with colorful buildings, and the town offers plenty of opportunities to explore local markets, museums, and colonial architecture.

  • Underwater Sculpture Park: For something unique, visit the underwater sculpture park near Molinière Bay. It's one of the world’s first of its kind, and a must-see for divers and snorkelers.

  • Sandy Island: Located off Carriacou, this small, uninhabited island is perfect for a day of snorkeling or just relaxing on the beach. The surrounding coral reefs are teeming with marine life, offering excellent snorkeling.

  • Don't miss - Happy Island - a man-made conch shell island located by Union Island of St. Vincent & The Grenadines. Access to the island is only possible by dinghy, and it is the perfect spot to enjoy sunset cocktails!

5 Best Caribbean Destinations to Charter a Boat
Happy Island, Union Island, St. Vincent & The Grenadines
  • Local fishermen will approach you while trying to anchor to offer a variety of services: a mooring ball rental, garbage disposal, fresh fish and shellfish caught during the day, fresh bread in the morning etc. These people are lovely and helpful, and the prices are not too dear (of course haggling is sometimes required :-)). Don't miss out on this experience!

5 Best Caribbean Destinations to Charter a Boat
Local fishermen, Carriacou, Grenada

Sailing Tips

  • While Grenada is a fantastic spot for seasoned sailors, novices should be aware of the changing winds and potential for strong currents in some areas.

  • Many sailors start or end their journey in Grenada to explore the nearby St. Vincent & The Grenadine, making it a great starting point for longer trips. Be aware of the local maritime regulations, especially when traveling between different territories.


5 Best Caribbean Destinations to Charter a Boat
Les Saintes, Guadeloupe

4. Guadeloupe

Why It's Great for Winter Sailing

Guadeloupe is comprised of 5 islands, the largest is shaped like a butterfly. It is a part of the French Caribbean and offers a mix of rich culture, beautiful landscapes, and protected anchorages. Winter temperatures range between 75°F and 85°F, with moderate trade winds making it ideal for sailing. The island’s biodiversity, volcanic mountains, and colonial history offer plenty of onshore activities when you’re not out on the water.


Key Highlights

5 Best Caribbean Destinations to Charter a Boat
Les Saintes, Guadeloupe
  • Les Saintes: A small group of islands south of Guadeloupe, Les Saintes are known for their crystal-clear waters, charming French villages, and secluded beaches. The anchorage here is well-protected, and the snorkeling is some of the best in the region.

  • Pointe-à-Pitre: Guadeloupe’s largest city, Pointe-à-Pitre, offers a taste of French culture mixed with Caribbean influences. It’s a great spot for shopping, dining, and experiencing the island’s vibrant markets.

  • La Soufrière Volcano: For the adventurous, a hike to the top of La Soufrière, an active volcano, offers breathtaking views of the surrounding islands. It’s an exciting land excursion that contrasts beautifully with days spent sailing.

5 Best Caribbean Destinations to Charter a Boat
Les Saintes, Guadeloupe

Sailing Tips

  • The sailing conditions around Guadeloupe are generally favorable, but be prepared for stronger winds on the eastern side of the island.

  • French is the dominant language here, so a basic understanding of the language can be helpful when interacting with locals.





5. Belize

5 Best Caribbean Destinations to Charter a Boat
Tobacco Caye, Belize

Why It's Great for Winter Sailing

While not in the Caribbean, Belize offers an entirely different yet equally stunning sailing experience, thanks to its extensive barrier reef system—the second largest in the world. The winter months provide calm seas, making it ideal for navigating the sheltered waters around the cayes and the reef. Belize’s rich marine biodiversity, coupled with Mayan ruins and jungles onshore, makes it a top destination for those seeking adventure and natural beauty.


Key Highlights

  • Placencia: This laid-back village on the southern coast of Belize serves as a gateway to explore the southern cayes and the Sapodilla Cayes Marine Reserve, which is known for its crystal-clear waters and unspoiled reefs.

  • The Hideaway Caye, by Pelican Caye - a private island owned and operated by Kim & Dustin, along with their young teenage daughter. The couple started to develop the island in 2009, and so far have built a few cabanas, a restaurant-bar, surrounded by beautiful wooden pathways and bridges. The restaurant offers deliciously cooked fresh meals featuring local catch of the day. Reservation is needed - see information on their website.

5 Best Caribbean Destinations to Charter a Boat
The Hideaway, Pelican Caye, Belize

Sailing Tips

  • Navigation in Belize requires careful attention to the coral reefs and shallows. Charts and local knowledge are essential to avoid running aground.

  • Winter sailing in Belize is generally calm, but the open waters outside the barrier reef can present more challenging conditions for less

    experienced sailors.





To summarize, sailing during the winter months is an excellent way to escape the cold and immerse yourself in the tropical beauty of some of the best boating destinations in the world. Whether you're exploring the sheltered waters of the British Virgin Islands or navigating the coral reefs of Belize, these five destinations offer a perfect mix of adventure, relaxation, and stunning natural landscapes. Each location presents unique challenges and rewards, making them perfect for sailors of all skill levels. So, dust off your sea legs, book your charter, and set sail for a winter adventure you'll never forget.

5 Best Caribbean Destinations to Charter a Boat
Snorkeling in Placencia, Belize

Ready to book your next charter in the Caribbeans and get more tips and information?

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