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.

Join the Island Girls for a week-long party on Fleet Week! We have so much to celebrate that you won't want the fun to end!

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.

Sail on our Rum Cruise and learn the history of rum, how it’s made, and how to mix the perfect rum cocktail!

FLEET WEEK

Tropical Temptations
Home Port St. George’s, Grenada
Carriacou | Mayreau | Tobago Cays

Anchors aweigh for Fleet Week! A week-long celebration in the Windwards! Boat races, deck parties, beach bonfires, and wait for it… a Jammin' Jump Up Retro Night! We'll dust off that crazy hat and tacky tourist shirt and show 'em how we used to party… and still can!

DIAMANT | VELA

2025
November 2 - 8, 2025
and
November 29 to December 5, 2025

Boat races, beach parties, bananas!

RUM CRUISE

Pitons and Paradise
Home Port Rodney Bay, St. Lucia
ST. LUCIA - Anse Chastanet | Pigeon Island
MARTINIQUE - Grande Anse D’Arlets | Pt Anse D’Arlets | St Pierre

Born to rum? Join us and 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 overproof!

Sail to islands where traditional distilling methods are still used to produce some of the world’s finest rums.

Hosted by our very own rum-ologist Dave Russell.

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

VELA

2025
December 14 - 20, 2025