The Caribbean

sailing holidays

Sailing experience level

Tropical island bliss at your fingertips

Discover islands rich in colonial history and picturesque ports aboard a monohull or catamaran charter in the Caribbean. Composed of over 5,000 islands, reefs and cays and combining easy line-of-sight sailing and challenging open water thrills, the Caribbean is a veritable sailor’s playground. And with secluded white-sand beaches studded with coconut palms, picture-perfect harbours alive with splashes of island colour and isolated coral reefs framed by a backdrop of mesmerising blue, you’ll be spoilt for places to play.

Where will you go on holiday? With breath-taking Caribbean charter destinations like Antigua, Bahamas, Belize, British Virgin Islands, Grenada, St. Lucia and St. Martin, you’ll create picture-perfect memories that last a lifetime.

Our Bases in the Caribbean

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
The Bahamas

Abacos, Bahamas

  • Beautiful beaches
  • Famous wreck dive spots
  • Blissed-out year-round sailing
Experience level 2
Explore Abacos, Bahamas

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

Antigua sailing holidays

  • Excellent wreck and reef diving
  • Blue water sailing in steady trade winds
  • A stunning beach for each day of the year
Experience level 2
Explore Antigua sailing holidays
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

Grenada sailing holidays

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

Your Caribbean Holiday, Your Way

Choose from a bareboat charter, flotilla holiday or a skippered charter holiday in the turquoise waters of the Caribbean. Exciting blue water passages await you on your next sailing adventure. Take short island hops or cruise in calm, protected waters in a monohull or catamaran of your choosing.

Caribbean bareboat charter holidays

Independently set sail on a bareboat charter in the Caribbean and you’ll have your pick of anchorages and moorings in tropical paradise. With each destination boasting different amenities and activities, you’ll never be bored by the Caribbean’s charm and beauty. Whether you’re a beginner or advanced sailor, you’re sure to find a balance of easy line-of-sight sailing and adventurous open water thrills in your monohull or catamaran.

Caribbean flotilla holidays

Share new adventures with new friends you holiday in the Caribbean on a flotilla. When you go on a flotilla holiday in the British Virgin Islands, you’ll party on water and on land. Spend your days exploring dive sites or kayaking, then savour flavours from around the world at a number of restaurants and bars.

Skippered Caribbean charter holidays

Skippered charters aren’t just for beginners. If you want to brush up on your sailing skills or simply let a skipper guide the way, then a skippered charter holiday gives you the best of both worlds. Licensed skippers are available for the day or choose for a skipper to be your guide throughout the duration of your trip. Enjoy the spectacular sights of the Caribbean at the pace you choose.