The Caribbean

Sailing holidays

1-3
Sailing experience level

Tropical island bliss

Close your eyes and imagine your next holiday sailing the Caribbean in your own monohull or catamaran. The warm, salty air awaits you. Will you set your sights on the pristine beaches of Antigua, soar through rainforests on a zipline in Belize, or simply relax by taking in rays from atop your sun-washed deck?

The 5,000 islands, reefs and cays comprising the Caribbean are easily navigated. Hop from St. Lucia to Grenada, go diving in Tortola, or explore ancient Mayan ruins in Belize. The Caribbean islands offer an alluring mix of history and beauty you won’t find anywhere else in the world. Realise your nautical dreams aboard a monohull or catamaran charter in the Caribbean.

Our Bases in the Caribbean

Tortola, BVI

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore Tortola, BVI
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
Antigua

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

Belize

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

Grenada

  • 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
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Our charter types

If you want calm, protected waters and short island hops or exhilarating blue water passages, we offer a Caribbean sailing holiday to suit your sailing level. Charter a monohull or catamaran when you book a bareboat holiday. We offer flotilla holidays and skippered charters as well. Whether you want to sail your own boat or have a licensed skipper sail your boat, we offer the most popular charter types.

Caribbean bareboat charter holidays

Explore famous diving sites in Bahamas or stroll the romantic shores of St. Lucia by monohull or catamaran. Set sail on a bareboat charter in the Caribbean for the best adventures on and off land. Caribbean charter holidays combine amazing line-of-sight sailing with unique adventures for solo adventurers, couples, groups and families.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

20+
Stunning Sailing Destinations 
14
Flotilla routes
48
Types of yachts
44 yrs
Creating holidays
4 hr
Service guarantee
Consumer protection