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Meet the Captains Behind Windy City Sailing: Captain Josef & Captain Mike
- Ian Malanes
- Jun 30
- 4 min read
At Windy City Sailing, every charter aboard the Nebula is more than just a boat ride — it’s an experience crafted by two passionate individuals who share a deep love for the water, Chicago, and sharing the joy of sailing with others.
Behind the helm are Captain Josef Erlemann and Captain Mike, two men whose paths to Lake Michigan were different, but whose shared vision brought them together to create unforgettable sailing adventures for guests from around the world.
⛵ Captain Josef Erlemann – From Landlocked Roots to Life on the Water
Born and raised in Roscoe Village on the North Side of Chicago, Captain Josef didn’t grow up near the ocean or even on a lake, yet he found his calling in the wind and waves.
His journey into the world of sailing began not in Chicago, but in San Francisco, where he lived in the late 1990s. It was there, during his very first time stepping onto a sailboat on the San Francisco Bay, that everything changed.
💫 A Moment That Changed Everything
Josef still remembers the feeling as if it were yesterday, the gentle rocking of the boat, the crisp breeze in his face, and the vast openness of the water stretching out before him. In that moment, he felt something rare and powerful: freedom.
That initial experience sparked a lifelong passion. He quickly became enamored with the art and science of sailing, learning how to read the wind, trim the sails, and navigate the tides. The more he learned, the deeper his connection to the water grew.
Before long, what started as a weekend hobby turned into a serious pursuit. He pursued and earned his Captain’s License, determined to make sailing not just a part of his life, but his life's work.
🏙️ Bringing Sailing Back to Chicago
After years of sailing along the rugged California coastline, Josef returned to his hometown of Chicago, bringing with him both technical expertise and a renewed sense of purpose. He saw Lake Michigan not just as a body of water, but as a hidden gem waiting to be discovered by locals and visitors alike.
It was this vision that led to the founding of Windy City Sailing, where he could introduce others to the same peace and exhilaration he found on the water.
Today, Captain Josef leads each charter with enthusiasm, knowledge, and a deep respect for the sea. His calm demeanor, expert navigation skills, and ability to connect with guests make every voyage feel like a personal adventure.
⚓ Captain Mike – A Lifelong Love Affair with the Lake
While Captain Josef found sailing later in life, Captain Mike has always had a special relationship with Lake Michigan.
A retired Chicago firefighter, Mike has spent much of his life serving the city he loves. But even through decades of service on land, his heart remained on the water.
🌊 A Passion That Never Faded
Mike’s love affair with sailing began when he first stepped foot on a boat as a young man. Over the past 20 years, that early fascination has evolved into a full-fledged passion.
He has been an integral part of Windy City Sailing since its inception, helping shape the company into what it is today, a premier luxury sailing charter business offering unforgettable experiences on Lake Michigan.
There’s something about being on a sailboat, Mike says, that cannot be described. “You can feel the energy of the lake,” he explains. “When the sails catch the wind and you start moving, it’s like nothing else matters.”
🧭 More Than Just a Captain
With over two decades of sailing experience under his belt, Captain Mike brings not only skill but also a deep understanding of what makes a great sailing experience. Whether it’s guiding a group of first-time sailors or hosting seasoned boaters, Mike ensures every guest feels welcomed, safe, and inspired.
His warm personality and steady presence make him a favorite among repeat guests, many of whom return year after year specifically to sail with him.
🤝 A Perfect Pairing: Two Captains, One Vision
Though their journeys to Windy City Sailing took different paths, Josef and Mike share a common mission: to share the magic of Lake Michigan with as many people as possible.
Together, they bring a balance of technical expertise, storytelling charm, and genuine hospitality to every charter aboard the Nebula. Their combined experience and dedication have helped build Windy City Sailing into one of Chicago’s most beloved sailing charter companies.
🌟 What Makes Them Special
Captain Josef brings a meticulous eye for detail, a love for the mechanics of sailing, and a quiet confidence that puts everyone at ease.
Captain Mike brings warmth, humor, and a deep-rooted connection to the lake, making every trip a memorable story.
Whether you're celebrating a romantic anniversary, hosting a corporate event, or just looking for a new way to see the city, you’re in good hands with these two seasoned skippers.
🌅 Why They Do It
For both captains, sailing isn’t just a job, it’s a lifestyle. It’s about creating moments that matter, forging connections, and showing people a side of Chicago few ever get to see.
They’ve watched couples say “I do” on the deck of the Nebula, toasted anniversaries under the city skyline, and introduced countless guests to the thrill of harnessing the wind. And through it all, they’ve remained grounded in their love for the craft and the city they call home.
🛥️ Final Thoughts
From a boy from Roscoe Village discovering freedom on the San Francisco Bay to a retired firefighter finding peace on Lake Michigan, the story of Windy City Sailing is one of passion, perseverance, and purpose.
And with Captain Josef and Captain Mike at the helm, every guest gets to be part of that story.
So, whether you're setting sail for the first time or returning for your tenth charter, know that you're not just going on a boat ride, you're joining a legacy of two captains who truly love what they do.
Ready to meet the team and experience the Nebula for yourself?
👉 Book your private charter today and let our captains show you the beauty of Chicago from the water.
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