Island Windjammer Cruises

Island Windjammers Theme Cruises

We’ve taken something that’s already awesome and made it even better, by spicing things up with our popular Theme Cruises. Sail on a Rum Cruise and learn all about your favorite libation from a rum expert. Walk the plank, and say "Arrr!" to your hearts content, on a Pirate Week adventure. If beer is your thing, join the Island Hops Beer Cruise, and learn all about local brews and ciders. Want to sail solo but not alone? Take a Solo Sojourn, an exclusive sailing for solo travelers. And finally, we aren’t kidding about spicing things up! Have a taste of local fruit and vegetables and explore local markets with our professional chefs on a Taste of the Islands cruise!

Taste of the Islands Food Cruises

DISCOVER the flavors of the tropics.
EXPLORE island spice markets.
LEARN all about the locally grown fruits and vegetables.
ENJOY cooking demonstrations by our expert chefs.
For FOODIES, and those who want to get a taste of the islands.

SAGITTA July 22 – 28, 2018
Windward Islands Sails St. Lucia to Grenada
Home Port Marigot Bay, St. Lucia
Visit Mayreau  |  Bequia  |  Tobago Cays  |  Carriacou  |  Union Island

Pirates and Mermaids Week

Sail the Grenadines, roundtrip Grenada, on this epic adventure. There be spice islands, and rum. Swashbuckling contests, and rum. Legends, lore, and rum. It’s safe to say we know where the rum’s gone!

VELA October 28 - November 3, 2018
EMBARK | Grenada

Bequia  |  Carriacou  |  Mayreau  |  Tobago Cays  |  Union Island


Sagitta’s Solo Sojourns

Our Solo Sojourn cruises are exclusively for Solo Sailors like you. Comfortable in your own skin, you enjoy unencumbered travel, good food, exploring new destinations, learning about different cultures, and meeting like-minded active travelers. No couples, no children, no one to please or keep up with but yourself! Travelling on your own terms is liberating and fun, especially when sailing with Island Windjammers!

SAGITTA April 22 - 28, 2018
British Virgin Islands Round Trip Tortola
Home Port Road Town, Tortola
Visit Virgin Gorda  |  Norman Island  |  Cooper Island  |  Jost Van Dyke

SAGITTA December 2 - 8, 2018
Leeward Islands Round Trip St. Maarten
Home Port Philipsburg, St. Maarten
Visit Anguilla  |  Nevis  |  St. Barths  |  St.Kitts  |  St. Maarten

Online booking disabled. Call to reserve. 877.772.4549


Rum away with Island Windjammers and your host, noted rum expert Dave Russell of Rum Gallery on a Rum Cruise. Learn the history of rum, how it’s made, and how to mix the perfect rum cocktail. Sample premium whites, darks, aged, spiced, flavored and even a wee bit of over-proof! Sail to islands where traditional distilling methods are still used to produce some of the world’s finest rums.

For rum connoisseurs or those who just like to drink it!

VELA October 22 - 28, 2017
VELA November 4 – 10, 2018
French West Indies Round Trip St. Lucia
Home Port Marigot Bay, St. Lucia
Visit Dominica  |  Iles des Saintes  |  Marie Galante  |  Martinique

Cruise rate includes daily samplings of some of the world’s most exotic rums, and all other rum-related activities hosted by Dave Russell.

Island Windjammers does not promote over-consumption of alcohol. Please practice responsible sipping.

Island Windjammers