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.

Show off your mermaid tail, walk the plank, and say "Arrr!" to your heart's content, on a Pirate and Mermaids 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.

Our Yoga Retreat includes workshops on mindfulness, essential oils and morning and evening practices. Join all three 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!

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.


DIAMANT October 14 - 20, 2018

Windward Islands
Round Trip Grenada
Mayreau  |  Bequia  |  Tobago Cays  |  Carriacou  |  Union Island

A sampling of offerings:

Mornings start with energetic vinyasa flow, to ignite your day. Evenings wind down with a restorative yin, hatha, or yoga nidra, to restore and let go. Workshops explore the chakras, wellness through essential oils, and sound bowl meditation.

Deepen your yoga practice with your hosts, Carolina Salazar and Sarah Franco

Share cabins available. Vegetarian meal options.

Anchors aweigh for

Fleet Week is a week-long celebration when Diamant, Sagitta, and Vela will sail together in the Windwards! Boat races, deck parties, full moon 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!

October 21-27, 2018


Windward Islands
Round Trip Grenada
Mayreau  |  Bequia  |  Tobago Cays  |  Carriacou  |  Union Island

Boat races, beach parties, bananas!

Taste of the Islands
Caribbean Food Cruise

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.

VELA September 29 - October 5, 2019
Windward Islands Roundtrip Grenada
Home Port St. George’s, Grenada
Visit Bequia  |  Mayreau  |  Carriacou  |  Tobago Cays  |  Union Island

Pirates and Mermaids Week

Sail on an epic swashbuckling adventure. There be spice islands and rum. Costume contests, and rum. Legends of mermaids, pirate lore, and rum. It's safe to say we know where the rum's gone!

VELA October 28 - November 3, 2018
Windward Islands Sails Grenada to St. Lucia
Home Port Grenada
Visit 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 December 2 - 8, 2018
Northern Leeward Islands Round Trip St. Kitts
Home Port Frigate Bay, St. Kitts
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 November 4 – 10, 2018
French West Indies Round Trip St. Lucia
Home Port Rodney Bay, St. Lucia
Visit Guadeloupe  |  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 Hops Beer Cruise

Island Windjammers + West Indies Beer Co. Have joined together to bring you Vela’s Island Hops Beer Cruise!

If you have a thing for Natural Blondes, or have tipped a Drunken Goat while sharing a pint of Rogue Pirate… then you know your West Indies Beer. If you haven’t, it’s time you learned about these, and many more craft beers and ciders of the Caribbean!

Mark and Jill Heath — our hosts, and proprietors of the West Indies Beer, Co., will compare styles, different hops, yeast, and malts — and explain how and why they change beers.

We’ll even brew and name our own ale on our 6-day sail!

VELA October 14 - 20, 2018
Windward Islands Roundtrip Grenada
Home Port St. George’s, Grenada
Visit Bequia  |  Mayreau  |  Carriacou  |  Tobago Cays  |  Union Island

Island Windjammers