Winter Sailing Holidays

Winter Sailing Holidays

Blow Away those January Blues

Cold days and dark nights are a world away in our warm winter destinations. Top up your tan and feel the warmth of the sun on your skin as you cruise some of the world’s most exotic sailing destinations.

Discover the captivating island culture of the Caribbean in St. Lucia or Belize, or visit Australia’s Whitsunday Islands to marvel at turtles, manatees, and giant tropical fish gliding below a shimmering cerulean ocean. Dine on delicious barbecued lobster in the Caribbean, snorkel above diverse coral reefs, and soak up the sun on some of the world’s best beaches. On a warm winter holiday, you’ll leave the memory of cold winter nights in your wake as you sail between island paradises and sip gin and tonics from the deck of your own yacht.

Our Warm Winter Sailing Destinations

Winter Sailing Holidays


  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins

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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

Join a sociable flotilla in the irresistible Caribbean for some therapeutic winter sun. 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.

Skippered charter holidays

Let a skipper do the hard work as you discover the world’s best cruising grounds from the comfort of your deck. 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. 

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