Island Windjammers Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises

Sailing ship, tall ship, schooner, clipper, barque…

A windjammer ship by any name is fabulous fun!

Windjammer ships are known by a variety of names. We’re okay with that, because no matter what you call her, a tall ship is graceful, romantic, sexy, and fun! There’s no better way to island hop!

The minute you step aboard, the island rhythm takes over. Days are marked by sunrises and sunsets; how much or how little happens in between is completely up to you. That’s part of the charm of an Island Windjammers sailing holiday.

We set the course…you set the pace…sometimes the destination chooses for you. Some ports offer the best beaches and snorkeling, while others are known for their vibrant villages, rum shops, and quirky beach bars. Imagine waking up each day to a different island, and the promise of new adventure!

Life aboard is as casual and easy as an island sarong. Curl up on deck with a good book, or help the crew raise the sails. Lean on the rail, watch dolphins ride the ship’s wake, and count the enchanted islets dotting the horizon.

When night falls, shipmates gather to dance on deck, talk, laugh, and listen to the canvas snap and the rigging sing. Throw your head back with wild abandon. Kiss the stars, and wish the moon a sweet goodnight, for tomorrow is another day in your island life.

This is Island Windjammers...a style...a pace...a feeling.

What starts with a want, ends in a dare.

Face it—you need a vacation; a week or two to decompress and escape the stress and doldrums of everyday life. We’ve been there, and we know just what you need….pack a bag and sail away with us, to our islands in the sun.

Here, graceful palms shade you from the warm tropical sun, island breezes whisper sweet nothings, and sugar white beaches invite you to stay forever.

Here, you can swim like a damsel fish to coral reefs just off the beach, and wave hello to smiling seahorses and starfish, as swaying fans tickle your belly beneath the gentle waves.

Here, sparkly trinkets tempt and delight from the shops of funky seaside towns, and the local scene comes alive from your front row seat at a sidewalk café. Eat a mango, savor spiced rum, and get lost in the soulful rhythm of island life.

Here, tree frogs serenade, wild parrots call, and monkeys swing through the rainforest canopy. The scent of pink orchids intoxicates, and winding paths lead you to secret waterfalls.

What starts with a want, ends in a dare.

Dare yourself to dive in…and fall in love with life again.


  • Cruise Itineraries

Begin your adventure today! Call 877.772.4549 for reservations.