Barefoot Legacy

Windjammer Barefoot Cruises was a legendary small-ship cruise company founded in 1947 by Captain Mike Burke, a Florida-born entrepreneur with a love for the sea, adventure, and storytelling.

Starting with a single schooner named the Hangover, Burke built Windjammer into a cult-favorite travel brand known for its carefree attitude, rum-soaked evenings, barefoot dress code, and immersive sailing experiences across the Caribbean.

Unlike mainstream cruises, Windjammer's voyages were personal, bohemian, and deeply tied to the islands they visited. Guests hoisted sails, slept under the stars, and became part of the crew — all while exploring remote harbors, villages, and coves far from the beaten path. The experience was more floating camp than floating hotel, but that was precisely its charm.

Captain Mike was a charismatic, self-made showman who became a nautical folk hero. Known as the last true “American Pirate”, he wrote books, hosted parties on deck, and cultivated a fiercely loyal following that spanned decades. His motto “Don’t just take a cruise, sail an adventure!” became gospel for those who came aboard. His influence also shaped the Windjammer aesthetic: colorful, rough-edged, full of personality and heart.

At its peak, WBC operated a fleet of tall ships including the Polynesia, Yankee Clipper, Flying Cloud, Legacy, Fantome, and Mandalay. The company ran continuously for over 60 years, carrying thousands of passengers across turquoise waters in a way that no traditional cruise line could replicate.

Captain Mike passed away in 2013, and while his death marked the end of an era, the community he built remained fiercely connected. After financial troubles and the company’s closure in 2007, the spirit of Windjammer never died and the Mandalay became one of the last remaining vessels of that legendary fleet.

Thousands of former passengers — affectionately known as “Old Salts” — remain active in online communities, reunite in person, and share photos, stories, and toasts to the ships that changed their lives. Their passion is as alive as ever, and their devotion to the Windjammer legacy continues to fuel a movement. For them, Windjammer was never just a cruise — it was a way of life. Now we're bringing it back: The Windjammer Way.

Been carrying a Windjammer memory all these years? We’d love to hear it. Share yourTales from the Deck story here →