OUR STORY
From humble beginnings, Island Windjammers has grown into a leading independent small ship cruising company. IWJ was founded by shipmates, for shipmates. In 2008, CEO Liz Harvey brought together a small group of passionate investors who shared a love for authentic, relaxed, barefoot sailing adventures. Seeing a niche in the cruise industry for travelers seeking more personal, unhurried experiences, Island Windjammers launched its first voyage in 2009 aboard Diamant, the company’s first sailing ship.
Since then, we’ve been charting our own course and expanding our fleet and our horizons. Today, Island Windjammers proudly offers small ship cruises across a growing fleet of unique vessels, sailing to secluded hideaways throughout the Caribbean, Croatia, and Greece. What began as a dream to bring true adventure back to the sea has become a community of travelers who cherish the freedom, connection, and authenticity that only Island Windjammers can offer.
OUR MISSION
We believe that the best way to explore the Caribbean and Mediterranean is aboard a small ship. Our mission is to rekindle the romance and adventure of traditional sailing for those who crave more than an ordinary cruise – where the sea breeze, the sound of the sails, and the company of a few fellow adventurers sets the tone for something truly special.
We’re ideal for those shipmates who understand that when you cruise on a big ship, you’ll spend your whole time looking in. Adventure on a small ship, and you’ll spend your whole time looking out.
Get ready to… Escape. Explore. Exhale.
WHY CRUISE WITH ISLAND WINDJAMMERS
Small Ships, Big Adventures
Experience the magic of sailing on intimate ships where every voyage feels personal, not crowded.
Relaxed Travel, Remote Escapes
Our small ships slip into hidden harbors and iconic small islands that the big cruise liners can’t reach, letting you experience the Caribbean and Mediterranean the way they were meant to be: up close, authentic, and wonderfully laid-back.
Stress-free, All-Inclusive Cruising
Enjoy transparent pricing, freshly prepared meals, and friendly service with no hidden extras.
Trusted Since 2009
Proudly independent and sailor-founded, we’ve been delivering unforgettable small ship adventures since our very first cruise.
Sustainable by Design
From our zero-emission sailing ship to mindful travel practices, we’re committed to protecting the seas we love.
A Welcoming Sailing Community
Beginning with your first voyage, you’re not just a guest—you’re part of the Island Windjammers community. Board as strangers. Leave as friends.
OUR ETHOS
Our ethos is simple — Escape. Explore. Exhale. It’s the rhythm of every voyage we sail, and the promise behind every journey we offer.
ESCAPE.
Set Sail Your Way
Leave the crowds behind and rediscover the freedom of the open seas. Our small ship cruise fleet has something for every sailor. From a classic Caribbean schooner full of old-world charm, to sleek luxury yachts and even our brand new zero-emissions sailing ship, we are setting new standards for sustainable travel. Each ship has its own personality and story, but they all have some things in common: relaxed adventure, genuine connection, and the joy of life under sail.
EXPLORE.
Hidden Escapes & Iconic Shores
With Island Windjammers, you’ll explore the world beyond the big cruise ports. Our intimate sailing adventures take you to off-the-beaten-path islands and ports across the Caribbean, Croatia, and Greece — destinations chosen for their beauty, culture, and character. We’re growing every year, expanding our voyages to bring guests closer to the heart of each region we sail. From turquoise Caribbean coves to the sun-soaked coastlines of the Mediterranean, every stop is a story waiting to be lived.
EXHALE.
Relax, You’re Among Friends
Step aboard and leave the details to us. Since 2009, we’ve been trusted by travelers who value authentic small ship cruising with a personal touch. Our transparent, all-inclusive pricing and handy planning support means no surprises — just great company, and smooth sailing. With our Love For Sail Rewards Program, your loyalty starts paying off from your very first voyage. More than guests, our travelers are part of a tight-knit sailing community, and we’re grateful for every member who’s helped our ships feel like home at sea.
ESCAPE. EXPLORE. EXHALE.
This is more than our ethos — it’s your invitation to experience small ship cruising the Island Windjammers way.