Warm Winter Sailing Destinations

Sunny winter vacations

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 vacation, 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

The British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore The British Virgin Islands
Tobacco Cay Belize


  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins
Experience level 3
Explore Belize

St. Martin yacht charter

  • Blue water and coastal sailing
  • World-class diving and snorkeling
  • Glamorous resorts and laid-back beaches
Experience level 2-3
Explore St. Martin yacht charter

Grenada yacht charter

  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkeling
Experience level 3
Explore Grenada yacht charter
St. Lucia

St. Lucia yacht charter

  • Year-round trade winds
  • Unique, delicious local cuisine
  • Stunning mountainous, rainforest isle
Experience level 3
Explore St. Lucia yacht charter

Mahé, Seychelles

  • Remote, largely unexplored islands
  • Strong winds ideal for experienced sailors
  • Good diving, snorkeling and sport fishing
Experience level 3
Explore Mahé, Seychelles


  • Ancient fishing villages
  • Exotic beauty and idyllic islands
  • World-class diving and snorkeling
Experience level 2
Explore Thailand

Bareboat charter vacations

Take charge on a bareboat charter vacation. 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 vacation is just you, a beautiful yacht and the boundless ocean to explore.

Winter flotilla vacations

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 vacations 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 vacations

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.