Where to Sail in Winter: December, January & February

As the days get shorter and the air grows colder, it’s natural to dream of escaping to the open water. But you don’t have to wait for summer to answer the call of the sea. Winter sailing offers a unique opportunity to explore some of the world’s most stunning sailing destinations in winter, often with fewer crowds and ideal weather conditions. From the sun-drenched Caribbean to the tranquil waters of Southeast Asia, there are countless winter sailing locations waiting to be discovered. Whether you're planning a festive escape in December, a New Year's adventure in January, or a romantic getaway in February 2026, a winter yacht charter is the perfect way to trade snow for sunshine.

This guide will help you discover where to sail in winter, highlighting the best places to sail in winter and providing tips to help you plan your perfect escape. We'll explore how seasonal wind patterns create ideal sailing conditions and why a winter charter can be one of the most rewarding experiences for any sailor.

As the days get shorter and darker towards the end of the year, our thoughts tend to drift off to the delights of summer, to the carefree days spent sailing and swimming, or relaxing evenings at anchor in quiet bays. But fear not – the sailing season doesn’t have to stop when winter starts!

There's a great selection of simply gorgeous sailing areas spread slightly further afield that are well worth the trip between December and February. Here's our pick of the best places to get some winter sun sailing done.

December is when the Caribbean season really gets going; the trade winds have settled into a familiar pattern and the weather is very pleasant for the whole month. The region’s driest month is also among its coolest, but with an average temperature of 27˚C across the chain, it’s definitely not cold!

British Virgin Islands - The home of Caribbean cruising since the early 1960s, the British Virgin Islands have to be seen to be believed. A tight-knit group of over 60 gorgeous islands, all blessed with warm, consistent trade winds and ridiculous white sand beaches fringed by palm trees, the BVI is as close to yachting paradise as it’s possible to get. December is a great time to visit, when the weather is warm and settled, but before the rush of the holiday season over Christmas and the New Year. Set sail from Tortola and cruise across to the gorgeous coral island Anegada. Visit the legendary Soggy Dollar and Willy Ts bars. Dive one of the 70 incredible reefs and wrecks scattered around the sailing area. Sheer bliss. December breezes average 10-12kt ESE, with temperatures a wonderful 26˚C.

Whitsundays - Australia is famously hot in the European winter, and the Whitsunday islands are no different. These swirling sands are protected by the magnificent Great Barrier Reef, and although December is among the hottest months over there, strong 16kt ESE breezes bring a welcome cooling effect. One for the advanced sailors, with plenty of wind and interesting navigational challenges, as well as truly sensational diving.

The best way to beat the January blues and charge into the new year full of energy is to take a yacht charter holiday somewhere truly spectacular. January is a great time to explore off the beaten track, going to far-flung sailing areas that really offer something a little different to your average Mediterranean or Caribbean sailing holiday.

Belize - Meet howler monkeys, explore secluded cays and creole villages, and sail in flat seas, protected by a coral reef lying 15 miles offshore. A yacht charter holiday in Belize is coastal sailing, but not as you know it. An unspoilt Central American treat, complete with Mayan ruins, Belize is at its absolute best in January, with 25˚C averages and cooling 8kt easterly breezes.

Bahamas - Split into two distinct island groups, the Abacos and the Exumas, the Bahamas are a unique bridge between the Americas and the Caribbean. The chain’s geography creates a diverse ecosystem of coral reefs, cays , mangrove swamps, and rainforests. This wildlife haven is home to a unique collection of species, from sharks to swimming pigs, and filled with gorgeous sandy beaches. The Bahamas is at its most glorious in January, with air temperatures a very comfortable 28˚C, and great sailing breezes of 10-15kt the norm all month.

February’s flexibility makes it a very appealing time to go on a sailing holiday. The Caribbean sailing season is in full swing, with simply glorious sailing conditions all month long. Meanwhile, stable summer winds have settled in Southeast Asia, making this a perfect time to head east or west. February is ideal for a spot of sailing, diving and exploring the mystical jungles and friendly welcomes Thailand has to offer.

Antigua - Sail out of the famous Nelson’s Dockyard and skirt around Antigua’s beautiful coast, fringed by 365 beaches. Walk up Shirley Heights and join one of their famous 'jump up' steel band parties. February is warm (26˚C), windy (15-20kts), and sees 9 hours of daylight every day, with a magical sunset practically guaranteed each night. Sheer bliss on the water.

St Martin - St Martin is half Dutch half French, and full of cosmopolitan delights. Ideally located for trips to the neighbouring cluster of St Barth’s, Anguilla, and Saba, it’s easy to see why this is one of the most popular charter bases in the Caribbean. Temperatures are again nice and warm, with a little less wind than Antigua but still enough to cool down and get moving.

Thailand - The driest month of the year in Southeast Asia is also among the warmest, with temperatures averaging 29˚C. Having said this, humidity is relatively low, so the air is less stifling than other months, which puts February among the most comfortable times of year to sail the Andaman islands. The winds have settled throughout January into February, and tend to blow gently from the east, at 5-8 kts in the early months of the ye