Caribbean sailing


Sailing holidays

Escape the April showers

Wave goodbye to humdrum and head to the world’s most beautiful destinations on a spring sailing holiday. Spark something in your inner adventurer as you chase the sun to far-flung destinations and climb aboard a Sunsail yacht to experience the very best of springtime sailing.

Cruise the sparkling waters of the Caribbean Sea as you sail the idyllic islands of the Bahamas and BVI. Bask in the sumptuous climate of Grenada and enjoy island hopping and adventurous open-water passages in St. Martin, or head further afield to explore the remote islands and pristine white beaches of the Seychelles. Discover remote paradise islands and sip refreshing cocktails at beachside bars. Feel the wind in your sails as you tack and gybe in sparkling seas, and encounter exotic wildlife both above and below the water. 

Our springtime sailing destinations


Grenada sailing holidays

  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkelling
Experience level 3
Explore Grenada sailing holidays

British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore British Virgin Islands
St. Lucia

St. Lucia Sailing Holidays

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

St. Martin sailing holidays

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

Mahé, Seychelles

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

Bareboat yacht charter holidays

Strike out on your own on a bareboat charter holiday. Enjoy the freedom of the open ocean as you cruise some of our spectacular destinations, exploring at your own pace and calling wherever you choose. A bareboat yacht charter is the most exciting way to discover your chosen destination.

Flotilla sailing holidays

Join a springtime flotilla sailing holiday in the beautiful British Virgin Islands. You’ll join up with a group of flotilla adventurers for sociable on shore activities each evening, sailing at your own pace during the day as you explore the sunny BVIs. Be as sociable as you like or go your own way on a flotilla sailing holiday.

Skippered yacht charters

Hire a skipper this spring and explore a different side of the world’s best sailing destinations. Your skipper will take the pressure off, taking the helm and showing you the local highlights most visitors never get to see. Book your skipper for your entire holiday or just for a day or two, allowing you to improve your sailing skills and increase your confidence on the water under their expert guidance.