Guest Bio
Charles J Kropke is the CEO of The Windjammer Way, a company dedicated to reviving the tradition of intimate sailing travel in the Caribbean. An entrepreneur and environmental advocate, Charles has spent decades shaping sustainable tourism experiences that connect travelers with culture, history, and nature. His leadership at The Windjammer Way focuses on restoring historic schooners and supporting fragile island economies while offering guests authentic, windswept adventures.
Charles’s journey began in childhood with an early fascination inspired by vintage National Geographic magazines and the original Windjammer Barefoot Cruises. That lifelong interest has evolved into a commitment to preserving maritime heritage and fostering meaningful travel experiences. Beyond The Windjammer Way, he founded Dragonfly Expeditions, an eco-tour company in Florida, and oversees Tropic Moon Holdings, a portfolio of mission-driven businesses emphasizing sustainability and community impact.
Show Summary
In this episode of the Big World Made Small Adventure Travel Podcast, host Jason Elkins speaks with Charles J Kropke about his work revitalizing the iconic Windjammer sailing experience. Charles shares the story behind The Windjammer Way, a company resurrecting the spirit of classic tall ship cruises with their flagship vessel, the SV Mandalay, a 103-year-old steel-hulled schooner. Operating primarily in the Caribbean, their voyages emphasize small groups, cultural connection, and a relaxed, authentic atmosphere.
Charles reflects on his early inspiration from National Geographic and how that shaped his vision for sustainable and soulful travel. He describes the unique Windjammer culture where crew and guests blend seamlessly, with no televisions onboard and activities centered around storytelling, parties, and exploring remote islands. The conversation also touches on the challenges of restoring historic ships, navigating Caribbean itineraries with seasonal weather, and the company’s inclusive approach to travelers of all backgrounds.
Throughout the episode, Charles highlights his broader entrepreneurial path, including his eco-tourism company Dragonfly Expeditions and past collaborations with the Margaritaville brand. He invites listeners to reconnect with their inner child and consider the timeless appeal of wind-powered adventure as a new generation prepares to set sail.
Big World Made Small guest features are invitation-only and selected based on story, experience, and fit with the show. Guest support helps make the episode possible, but it does not determine who is featured. This helps keep the show free of third-party ads and interruptions while keeping the focus on real, story-driven conversations.
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