Five of the Best Caribbean Islands to Set Sail for in Winter 2023

The Caribbean is a sailor’s paradise, known for its crystal-clear waters, gentle trade winds, and stunning landscapes. With winter 2023 just around the corner, it’s the perfect time to plan your Caribbean sailing adventure. Whether you’re an experienced sailor or a novice looking to try something new, the Caribbean offers a plethora of islands to explore. In this article, we’ll introduce you to five of the best Caribbean islands to set sail for in winter 2023.


Known as the “Sailing Capital of the Caribbean,” Antigua is a top destination for sailors of all skill levels. With 365 beaches (one for each day of the year), Antigua’s coastline is a sailor’s dream. The island hosts the world-famous Antigua Sailing Week, a regatta that draws sailors from around the globe. You can explore secluded coves, visit historic Nelson’s Dockyard, and indulge in the local cuisine. The steady trade winds and protected bays make Antigua a sailor’s paradise.

2.British Virgin Islands

The British Virgin Islands, often referred to as the “BVIs,” is a haven for sailors. The archipelago is composed of 60 islands, each with its unique charm. From the bustling Tortola to the quiet and pristine Anegada, the BVIs offer endless opportunities for exploration. White sandy beaches, clear waters, and the “line-of-sight” sailing experience make this destination ideal for sailors who want a mix of adventure and relaxation.

3.St. Lucia

St. Lucia is not only known for its lush tropical landscapes but also its excellent sailing conditions. The island is an ideal starting point for sailors looking to explore the Windward Islands. Sailing from St. Lucia allows you to visit neighboring gems like St. Vincent, Bequia, and Grenada. The Pitons, two towering volcanic peaks, serve as iconic landmarks and are a must-see for sailors and landlubbers alike.

4.The Grenadines

If you’re looking for a tranquil and off-the-beaten-path experience, the Grenadines are an excellent choice. This string of islands and cays offers secluded anchorages, pristine beaches, and world-class snorkeling opportunities. The Tobago Cays, with its crystal-clear waters and abundant marine life, is a highlight of any Grenadines sailing trip.


While not typically considered a traditional sailing destination, Barbados is gaining popularity among sailors seeking an unconventional Caribbean experience. With its vibrant culture, lively music, and friendly locals, Barbados offers a unique sailing experience. The island has several marinas, and its central location makes it an excellent starting point for exploring the surrounding islands.

The Caribbean is a dream destination for winter sailors, offering diverse experiences for all levels of expertise. Whether you’re a seasoned sailor looking to race in regattas or a novice seeking tranquility in secluded coves, the islands of the Caribbean have something to offer. From the classic Antigua to the off-the-beaten-path Grenadines, the choices are as diverse as the islands themselves. As you plan your winter 2023 sailing adventure, keep these five Caribbean gems in mind for an unforgettable journey on the high seas. Fair winds and following seas!

Back to top button