Winter Sailing Holidays

When the darkest days of the year roll around, it’s time to escape to a glittering sea for some winter sun. If you’ve forgotten what the warm sunshine feels like on your skin, or how the sea air just makes you feel more alive, you’ll love our suggestions for the best places to take a winter sailing holiday. You’ll come back feeling revived and ready for spring.

Winter Sun Destinations

Trade the winter rush for sun-drenched beaches and crystal-clear waters. A Christmas sailing holiday is the ultimate way to unwind, far from the holiday crowds. Did you know that the best time to sail the British Virgin Islands is from December through to April, making the BVI a perfect destination for sailing at Christmas?

Grenada is another popular choice in the Caribbean for winter sun packages, but the weather is likely to be better for sailing in January, so plan your trip just after Christmas into the New Year. Here, and in other Caribbean destinations like Belize, you can dine on delicious barbecued seafood, snorkel above diverse coral reefs, and soak up the sun on some of the world’s best beaches.

Want to try another winter sun destination? Book a sunshine escape to our destinations in Southeast Asia, the Indian Ocean or the South Pacific. Visit Australia’s Whitsunday Islands to marvel at turtles, manatees, and giant tropical fish gliding below a shimmering cerulean ocean.

Winter Sun Sailing Holiday Destinations

Discover your perfect winter sun sailing adventure with our curated destinations, offering calm waters for beginners, vibrant cultures, and thrilling activities for seasoned sailors.

From the breathtaking beaches of the BVI to the hidden gems of St Lucia, explore our top winter sun sailing spots below and book your idyllic charter today.

Types of Winter Sun Holidays

We offer sailing holidays for sailors of all abilities and experience levels. Whichever destination you choose for your winter sun or Christmas sailing trip, you’ll have great options for charter types and extras.

Winter bareboat charter holidays

Take charge on a bareboat charter holiday. You’ll have the freedom to sail at your own pace and explore as much or as little of your chosen destination as you like, calling at quiet bays and bustling towns or simply enjoying the sensation of the ocean slipping away beneath your keel. A bareboat charter holiday is just you, a beautiful yacht, and the boundless ocean to explore.

Winter flotilla holidays

Sail with like-minded adventurers on a flotilla holiday in the Caribbean, where each day is a perfect mix of independent sailing and lively social gatherings. Explore the paradise islands of the BVI with a group of fellow flotilla adventurers, sailing alone or in groups by day and meeting up for fun social activities by night. Flotilla sailing holidays are perfect for families and groups, giving you the chance to improve your sailing skills and make new friends in the beautiful Caribbean sunshine – discover some of our top winter sun sailing destinations for families.

Winter skippered charter holidays

On a skippered charter holiday, you can relax and let an experienced skipper take the helm while you soak in the beauty of your surroundings. From hidden anchorages to off-the-beaten-path island gems, your sailing adventure is in expert hands. Improve your sailing skills with the help of an expert skipper, ready to take the helm when you need a rest and happy to step back and show you the ropes. You’ll benefit from local insights and advice, heading off the tourist trail to discover your destination’s hidden gems.

Embark on a winter sailing adventure

Benefits of Winter Sun Holidays

Make cold days and dark nights a world away by travelling to one of our warm winter destinations in December, January or February. Make it your New Year’s resolution to take some ‘you time’ to top up your tan and thaw off, and feel the warmth of the sun on your skin as you cruise some of the world’s most exotic sailing destinations.

A winter sun holiday is the perfect escape, offering a dose of vitamin D, brighter moods, and a chance to explore new destinations. Enjoy fewer crowds, lower off-season prices, and the opportunity to stay active with activities like swimming and water sports. Plus, it is the ideal time to relax, make memories, and soak up the warmth while leaving the cold behind.

Things to Do on a Winter Sun Holiday

A sailing winter sun holiday is the ultimate way to escape the chill and immerse yourself in tropical paradise. Swim in warm, turquoise waters or snorkel over vibrant coral reefs teeming with colourful marine life. For diving enthusiasts, many destinations offer world-class dive sites where you can explore underwater caves, shipwrecks, and abundant sea creatures. Each day brings the chance to anchor near secluded beaches, perfect for relaxing on soft sands or enjoying a private picnic.

Food lovers will relish the opportunity to savour fresh, locally prepared dishes. Whether it is a seafood feast at a beachfront restaurant or cooking on board with ingredients sourced from bustling local markets, the flavours of the region will enhance your journey. With every new island or coastal stop, you will discover breathtaking scenery, peaceful bays, and a variety of activities that make your sailing winter sun holiday unforgettable.

Winter Sun Holiday FAQ