Sunsail, Caribbean

Dominican Republic, Leeward Islands, Windward Islands, Virgin Islands/ Puerto Rico, Turks and Caicos


Starting at $1,000/week


Creating holidays for over 40 years

Tracing our heritage back to 1974, we are the world’s leading sailing vacation company, delivering unforgettable sailing adventures in some of the world’s best cruising grounds.

We first set sail from Aegina, on Greece’s exquisite Saronic Gulf, with just seven 25ft Snapdragon yachts. Led by Skipper Janet Green, her Australian hostie Megan and English engineer David Archer, the sailing vacation was so successful that seven more Snapdragons were built, making the first ever flotilla fleet.

Since those early days, we’ve developed bareboat routes and flotilla itineraries that take in the best of our destinations. Go your own way and explore to your heart’s content on a bareboat charter, or add a sociable twist on a flotilla, with the security, comfort and support of a lead crew just a VHF call away. From seven days of exciting sailing in the Saronic to two weeks on a chilled-out Caribbean adventure, we’ve got the world’s best cruising grounds covered.

All these years later, we’re just as passionate about sailing as we were when we first started. We offer bareboat charters in 20+ Stunning Sailing Destinations and flotilla sailing vacations in four countries, while our fleet has grown from seven to 538 yachts. We have also set up sailing schools around the world to share our knowledge and passion, and pass on the thrill we first felt over 40 years ago.

Whether you’re looking for a tailor-made sailing vacation, a skippered or yacht charter, a flotilla or a sailing course, we’ll look after you every step of the way.

Base Locations

The Americas, The Caribbean, United Kingdom, The Mediterranean, Seychelles, Thailand, South Pacific

Fleet Size


Sailing Area

Caribbean-Antigua, Bahamas, Belize, British Virgin Islands, Grenada, St. Lucia, St. Martin North America- Vancouver Meditteranean- Greece, Croatia, Mallorca, Italy Southeast Asia- Seychelles South Pacific- Tahiti, Tonga, Whitsundays Indian Ocean- Seychelles United Kingdon- Portsmouth


  • Sunsail 484- 4 Cabin
  • Sunsail Lagoon 464- 4 Cabin
  • Sunsail Lagoon 424- 4 Cabin
  • Sunsail 404- 4 Cabin
  • Sunsail 444- 4 Cabin
  • Sunsail 454- 4 Cabin

View Sunsail, Caribbean Website


  • Sunsail 38- 2 Cabin
  • Sunsail 41- 3 Cabin
  • Sunsail 47- 3 Cabin
  • Sunsail 41.0- 3 Cabin
  • Sunsail 46- 3 Cabin
  • Sunsail 51- 4 Cabin

View Sunsail, Caribbean Website

Worldwide Yacht Charters


  • Alaska
  • Bahamas
  • Belize
  • California
  • Canada
  • Central America
  • Florida
  • Great Lakes
  • Mexico
  • New England
  • Pacific Northwest
  • South America


  • Antarctica
  • Arctic


  • Indian Ocean / SE Asia


  • Dominican Republic
  • Leeward Islands
  • Windward Islands
  • Virgin Islands / Puerto Rico
  • Turks and Caicos


  • Croatia
  • France
  • Greece
  • Northern Europe
  • Turkey
  • Western Mediterranean-Spain / Balearics
  • Western Mediterranean-Naples / Sicily
  • Western Mediterranean-Riviera / Corsica / Sardini

Middle East

  • Dubai
  • Red Sea
  • United Arab Emirates


  • Australia
  • French Polynesia
  • Galapagos
  • New Zealand
  • South Pacific
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