Planning to sail in December, January, or February without freezing?
Borrow A Boat has already what you need for your winter sailing destinations to actually work:
- Think steady trade winds that won’t leave you fighting storms.
- Think anchorages where you can drop the hook safely without dodging bad weather.
- Think marinas where you can refill water, grab fuel, and get a decent meal.
These are the winter sailing destinations where you can trust the weather patterns, enjoy warm water, and still find a lively bar or night market once you drop anchor. From Belize’s barrier reef to Tenerife’s volcanic coastline, every location here is chosen for what works for sailors, not just what looks good in a brochure.
You’ll get all the facts: the best months to go, realistic route ideas, what marina facilities are open, plus a few quirks like where to avoid crowded anchorages or tricky currents.
Table of Contents
Martinique – Short Island Hops
For sailors looking for convenience and reliability, Martinique offers one of the best winter sailing experiences in the Caribbean. With steady trade winds, warm weather, and excellent marina facilities, this French island is a comfortable and scenic base for island-hopping adventures. Le Marin, Martinique’s yachting hub, provides everything from sail repairs to fresh baguettes within walking distance. You can sail to St. Lucia in half a day or head north to Dominica for a more adventurous passage. Carnival season from February to March is a lively time to visit, but anchorages can become crowded, so it’s best to plan your arrival early.
Tenerife – Canary Islands’ Winter Basecamp
Tenerife is the go-to winter sailing hub for those seeking mild temperatures and steady northeast winds. Starting from Santa Cruz or San Miguel, sailors will find strong provisioning options and reliable maintenance facilities. The island’s location makes it easy to enjoy short hops to La Gomera for relaxed passages or venture further to La Palma and El Hierro for more challenging offshore legs. While the weather is generally favourable, the Atlantic swell can affect open anchorages, so it’s wise to keep a marina backup plan in mind. Tenerife combines practical sailing logistics with plenty of onshore attractions, from volcanic landscapes to lively coastal towns.
Belize – Barrier Reef Cruising
Belize delivers one of the most relaxed and protected winter sailing environments in the world. During the dry season from November to May, mornings are calm, breezes are consistent, and the barrier reef shields most sailing routes from heavy seas. This makes for easy day sails between the country’s many cayes, each offering its own unique charm. Caye Caulker is a favourite stop, with sandy streets, laid-back beach bars, and a “no cars” policy that adds to the island’s charm. However, sailors should note that charts can be outdated, so having a skipper or local knowledge is highly recommended when navigating through reef passages.
Mexico – Caribbean Coast Adventures
Mexico’s Caribbean coast is an increasingly popular winter sailing playground, with bases in Cancún, Playa del Carmen, or Cozumel allowing sailors to reach open water within an hour of arrival. The dry season from December to April brings predictable northeast trade winds and warm, clear waters perfect for diving and snorkelling. Isla Mujeres is an ideal layover spot, offering a sheltered anchorage, good restaurants, and resupply facilities. While the sailing here is enjoyable, marinas can be limited outside the main hubs, so careful planning for fuel and water top-ups is essential. This coastline combines reliable sailing with the vibrancy of Mexican culture and cuisine.
Antigua – Beaches, Regattas, and Marina Buzz
Antigua is a winter sailing hotspot, particularly during the island’s peak season, which coincides with major events like Antigua Sailing Week in late April. English Harbour stands out as a base that’s both historic and fully equipped, offering full-service docks, chandleries, and plenty of shore-side activity. Short passages north to Barbuda reveal pristine beaches, while longer runs to Guadeloupe provide more varied sailing challenges. Anchorages can fill quickly during regatta season, so early arrival or advance booking is key. Antigua strikes a perfect balance between excellent sailing conditions and an active social scene ashore.
Grenada – South Caribbean Gateway
Grenada offers a quieter but equally rewarding winter sailing experience for those seeking reliable winds and a relaxed pace. From December to April, sailors enjoy consistent breezes, low rainfall, and sheltered bays along the island’s south coast. St. George’s, the capital, provides nightlife, markets, and safe berths, as well as being a launch point for exploring the Grenadines. The sail to Carriacou or Union Island typically takes 4–6 hours, offering a pleasant passage with plenty to see along the way. It’s worth stocking up in Grenada before heading north, as provisioning options become more limited the further you go.
Where to Find the Right Balance
Not every party island offers great winter sailing, and not every excellent sailing spot has nightlife worth staying for. Antigua delivers both consistent trade winds and energetic shore-side atmospheres. Belize and Grenada lean towards the quieter side, but each has key nights and local events worth timing your trip around. Choosing the right route comes down to knowing your priorities winter is too short for bad anchorages or ports that don’t inspire you.
Each island offers something special, whether it be amazing hiking trails, breath-taking beaches or unique coasts to explore. The islands are warm and sunny all year, maintaining a temperature in the high 20s, and the culture and scenery you’ll discover is inimitable. Cape Verde is a great place to escape the winter tourism rush of other popular destinations.
Winter’s your chance to sail warm seas and maybe enjoy a drink or two at the dock. Pick your route. Check the season. Book your boat with Borrow A Boat.