Meet Our Team
The Windjammer Way
June 1, 2025
Charles Kropke, CEO
Charles is an entrepreneur, author, and environmental visionary with a decades-long career dedicated to reimagining how we experience the world. As the CEO of The Windjammer Way, Charles leads a bold movement to restore the romance and purpose of intimate sailing travel — offering guests windswept, soulful adventures in far-flung ports while supporting fragile island economies and preserving historic working schooners.
His love for this mission began in childhood, when he first discovered the original Windjammer Barefoot Cruises through vintage National Geographic magazines. Enchanted by the photographs and poetic spirit of the sea, he became a lifelong admirer of the ships and the company behind them, especially the iconic schooner Mandalay. That early fascination became a driving force throughout his life, culminating in his leadership today as he brings the vision back to life for a new generation of travelers.
Charles’s broader work spans sustainable tourism, cultural preservation, and creative enterprise. He is the founder of Dragonfly Expeditions, an award-winning eco-tour company that immerses travelers in the authentic history, landscapes, and communities of Florida and beyond. Through Tropic Moon Holdings, he oversees a diverse portfolio of mission-driven businesses focused on sustainable development, environmental innovation, and community impact.
Whether leading a tour through Florida’s backwaters or reviving the golden age of wind-powered exploration, Charles blends deep local knowledge with global vision. His work is rooted in a simple but powerful philosophy: travel should enrich not just the traveler, but the places and people that make it possible.
Zack Luttrell, President
Zack is a serial entrepreneur and operations visionary with a deep-rooted talent for turning bold ideas into unforgettable experiences. As President, COO, and Co-Founder of The Windjammer Way, Zack is the driving force behind the brand’s logistics, partnerships, and execution.
A master of operational strategy and community-building, Zack brings over two decades of experience in domestic and international sales, experiential marketing, and business development. He is best known as the founder of Roaring Riot, Sports Fans Travel and Conquest Experiences, each groundbreaking fan engagement platforms that redefined the way sports communities rally around their teams — proving his knack for cultivating loyal, passionate audiences and rooted in his belief that travel should connect people, spark stories, and strengthen communities.
Whether he’s launching an immersive cruise brand or orchestrating large-scale fan travel experiences, Zack operates at the intersection of culture and commerce; blending strategic foresight with a talent for creating emotionally resonant events.
A decisive leader, creative thinker, and gifted connector, Zack is as comfortable charting a five-year strategic roadmap as he is jumping in to solve a last-minute logistics puzzle. His operational discipline and business-building savvy ensure The Windjammer Way delivers on its promise: to rekindle the romance and adventure of life under sail while preserving the heritage of historic ships and the communities they serve.
Taylor Bradley, Marketing Director
A strategist, storyteller, and systems thinker, Taylor has spent the last decade building brands across borders and industries. Having lived in many countries (currently in Portugal), she brings a global perspective to our team, architecting marketing strategies that are as thoughtful as they are scalable.
Before joining The Windjammer Way, she led global marketing efforts for fast-growing start ups and mission-driven companies – spanning deep-tech AI tackling textile waste at the source, renewable energy ventures across sub-Saharan Africa, and even a chapter as an educator in China. Across each role, Taylor’s professional passion has centered on the intersection of environmental impact, intentional design, and communications that drive meaningful action.
But as a wanderer herself, Taylor is just as personally passionate about authentic, ethical travel and the power of cultural exchange. That’s what drew her to The Windjammer Way: it was too crazy, too daring, and too wonderful not to say yes.
She sees this voyage — both professional and literal — as a rare, high risk, high growth, high reward opportunity. Because there’s something about a sailing ship that awakens something timeless in all of us. And there’s something about the experiences the Mandalay will offer that promises core memories to last a lifetime. According to Taylor, in this world, everyone deserves to sail away. Especially in paradise.
Boston Brown, Head Chef
Boston has been part of the Mandalay's family since the 1970s, long before hashtags and handheld GPS. Born in Jamaica and raised in kitchens where flavor was a kind of storytelling, he’s a culinary craftsman with a deep sense of tradition, pride, and play. His food is bold, local, and improvisational — drawing on Caribbean roots, sea-foraged ingredients, and decades of service at sea.
Boston isn’t just the Executive Chef. He’s the memory-keeper of the Windjammer fleet. He once served on the infamous Fantome, and he's seen more waves, storms, and dancing barefoot guests than anyone else on board. When the Mandalay was abandoned, he didn’t leave. He stayed. He guarded her hull. He swept her decks. He protected what she meant — even when no one was looking.
Now, as she comes back to life, so does he.
Because this ship isn’t just his workplace; it’s his home, his history, and his heartbeat.
Mashup Thompson, Head Bartender
If Boston is the soul of the ship, Mashup is the spark. Originally from St. Vincent, he joined the Mandalay in 1990 and has been lighting up her decks ever since. As Head Bartender, storyteller-in-residence, and impromptu DJ, Mashup is the vibe architect — a magnetic presence who knows how to lift spirits (literally and emotionally) even in the middle of a storm.
To the crew, he’s family. To the ship, he’s energy. To the passengers who remember him from the old days, he’s a legend.
When the company shut down, Mashup didn’t vanish. Like Boston, he stayed behind — guarding, caring, waiting. Because for Mashup, the Mandalay is more than a schooner. It’s where he grew into who he is. It’s the stage for his laughter, the echo of his island stories, and the place where he’s poured more rum than anyone in Windjammer history.
Now, he’s ready to pour again.
Julian Peterson, Captain
Captain Julian is the real deal. Not just a licensed skipper, but a product of the Windjammer legacy from the inside out. Born and raised on the island of Bequia in St. Vincent and the Grenadines, Julian first joined Windjammer Barefoot Cruises in 1989 as a deckhand. What started as a job quickly became a calling.
Over the years, he rose through the ranks the old-school way, from deckhand to bosun to 2nd mate about the Flying Cloud to 1st mate to finally becoming Captain of the Yankee Clipper from 2001 to 2007.
Julian has stood watch through midnight storms and glowing sunsets. He’s trained generations of crew, kept ships steady in rough waters, and always led with quiet confidence. His authority doesn’t come from shouting orders; it comes from knowing the ship, knowing the sea, and earning the trust of everyone aboard.
Now, with the Mandalay rising again, Captain Julian brings hard-won expertise and emotional ballast to a project that’s deeply personal. For him, this isn’t just a restoration — it’s a return to the helm of a way of life. A second wind.
