Island Windjammers

Crewed sailing vacations in the Caribbean

giant sailboat in the water

About Island Windjammers


When you’re looking to charter, a majestic 156’ classic sailing ship may not be the first thing that comes to mind. But now that we have your attention, we may be exactly what you’re looking for! Island Windjammers offers three fully crewed sailing vessels in the Caribbean, accommodating 10 to 26 guests. 


6 and 12-night itineraries are offered year round, covering the Eastern Caribbean from Tortola in the British Virgins, to Grenada in the Windwards. 


Each of our ships features plenty of deck space for dining al fresco and socializing. Below deck, you’ll find comfortable, air-conditioned accommodations with full bathrooms. 


A typical sail includes daily port stops with plenty of time ashore to snorkel, hike, shop or laze the day away. All meals are provided, along with beverages, beer, wine, and rum punch. Take your turn on the ship's rope swing, or take an evening dip in the warm Caribbean, illuminated by the ships underwater lights.


Not ready to charter? Island Windjammers accommodates solo sailors, couples and small groups. 


Chartering an Island Windjammers boat is as easy as a summer breeze. We offer all-inclusive net rates on request. No need for stressful negotiations or wondering if you’re getting the best price. 


Give us a call for more information. We’re standing by to assist!

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2019 Ships & Rates

Diamant - 10 Guests - from $22,400 net  

Sagitta - 24 Guests - from $44,800 net  

Vela - 26 Guests - from $52,800 net  


Call for 2020 rates


Charter Information

Charter Types: Crewed Charters    

Boat Types: Monohull Sailboats           

Fleet Locations: BVI, French West Indies, Leeward Islands, Windward Islands

  • beach with palm tree
  • table of food
  • man carrying plate of food

Sail With Island Windjammers

Charter Destinations

Cabin room

British Virgin Islands   

Road Town, Tortola, Cooper Island, Jost Van Dyke, Norman Island, Virgin Gorda


French West Indies   

Rodney Bay, St. Lucia, Dominica, Martinique, Guadeloupe, Iles des Saintes, Marie Galante


Northern Leeward Islands  

Frigate Bay, St. Kitts, St. Maarten, St. Barts, St. Kitts, Nevis, Anguilla


Southern Leeward Islands  

Frigate Bay, St. Kitts, Antigua, Motserrat, Nevis, Guadeloupe


Windward Islands  

St. George's, Grenada, Bequia, Carriacou, Mayreau, Union Island, Tobago Cays


Contact Us

Phone: (877) 772-4549        

Email: info@islandwindjammers.com  

Website: islandwindjammers.com


Social: Facebook | Instagram 



Ready to Plan a Charter?