The Caribbean

Sailing holidays

Sailing experience level

Tropical island bliss

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.

From the 700 islands of the Bahamas to the 365 beaches of Antigua; the lush, tropical island of St. Lucia to the European flair of St. Martin; the shipwreck dive sites of Tortola to the exotic jungle beauty of Belize, sail the Caribbean and realise your nautical dreams.

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

The Bahamas

  • Beautiful beaches
  • Famous wreck dive spots
  • Blissed-out year-round sailing
Experience level 1
Explore The Bahamas

St. Martin

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


  • 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


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


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

St. Lucia

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

Our charter types

Choose from bareboat yacht charters, flotilla holidays or skippered charter holidays in the Caribbean. Whether you want calm, protected waters and short island hops or exhilarating blue water passages, we offer a sailing holiday to suit your sailing level.

Caribbean bareboat charter holidays

From the romantic and welcoming shores of St. Lucia to the world-famous dive sites of the Bahamas, set sail on a bareboat charter in the Caribbean and you’ll have your choice of marinas, anchorages and moorings in locations that suit your individual taste. You’ll find a spectacular balance of easy line-of-sight sailing and adventurous open water thrills for that perfect sailing holiday where whatever you say goes.

Caribbean flotilla holidays

The most social way of sailing, a Caribbean flotilla holiday lets you spend your days dropping anchor amid the magical cays, bays and harbours, while your evenings can be spent with your flotilla sailing companions over dinner or drinking rum punch on the deck of your yacht.

Skippered Caribbean charter holidays

Brush up on your sailing skills or simply let your skipper be your guide, a skippered charter holiday in the Caribbean lets you have the best of both worlds. From the 365 beaches of Antiqua to the European flavour of St. Martin, your qualified skipper will show you the spectacular sights of the Caribbean at the pace you choose.

Choose Sunsail

Stunning Sailing Destinations 
Flotilla routes
Types of yachts
44 yrs
Creating holidays
4 hr
Service guarantee
Consumer protection