Our Crew
The Windy Escapes Difference
At Windy Escapes, we believe sailing is more than a boat ride—it’s an opportunity to connect with nature, unwind, and explore the beauty of Mackinac Island from the water. Whether you’re looking for a peaceful sunset cruise, a private sailing charter, or an unforgettable Great Lakes sailing experience, our small, experienced crew is here to make it happen.
Captain Mark Case
USCG Licensed OUPV Captain | Owner of Windy Escapes
With over 20 years of sailing experience, Captain Mark Case brings deep knowledge, steady leadership, and a lifelong love of the Great Lakes to every Mackinac Island sailing charter. A proud Marine Corps veteran, Mark discovered that sailing the open waters offers the peace and connection to nature he had been seeking after his service.
Mark founded Windy Escapes to share that experience—the joy of sailing, the wonder of wildlife, and the calm that comes from leaving the busy world behind. He’s not only passionate about sailing Mackinac Island’s beautiful waters, but also deeply involved in his community, coaching youth soccer and serving as a Boy Scout leader for many years.
Sailing with Mark isn’t just about reaching a destination—it’s about experiencing the magic of the Great Lakes, one unforgettable voyage at a time.
First Mate Kai Case
Experienced Sailor | Boating Safety Certified
Sailing runs in the Case family—and First Mate Kai Case is living proof. Kai has been on sailboats practically since birth, first cruising the Great Lakes at just three months old. By the age of 10, Kai was already teaching adults the ropes of sailing and has been Mark’s trusted right hand on board ever since.
Now a skilled and confident sailor, Kai serves as Mark’s right hand on every Mackinac Island sailing charter he can. With a calm presence, a sharp eye for safety, and a great sense of humor, Kai helps make each trip relaxing, fun, and memorable.