Crewed sailing vacations in the Caribbean
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!
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 Types: Crewed Charters
Boat Types: Monohull Sailboats
Fleet Locations: BVI, French West Indies, Leeward Islands, Windward Islands
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
St. George's, Grenada, Bequia, Carriacou, Mayreau, Union Island, Tobago Cays
Phone: (877) 772-4549