Your Mackinac Island Sailing Charter
Windy Escape isn’t just any Mackinac Island sailing charter—it’s the realization of a lifelong passion for sailing, nature, and the peaceful spirit of the Great Lakes. When you step aboard, you’re not just a passenger. You’re part of a tradition of adventure, tranquility, and unforgettable views that only sailing can offer.
Meet the Crew
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. With a calm presence, a sharp eye for safety, and a great sense of humor, Kai helps make each trip relaxing, fun, and memorable.
Captain John Fisher
USCG Licensed OUPV Captain | Crew Substitute
Captain John Fisher steps in when Captain Mark isn’t available, ensuring every Windy Escapes charter maintains the same high standards of safety and professionalism. As a licensed captain and experienced sailor, John also joins the crew as First Mate when needed, making sure your private sailing charter is smooth, enjoyable, and stress-free.
The Windy Escapes Difference
A Mackinac Island Sailing Charter Rooted in Experience and Passion
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.
Ready to Sail?
Let’s leave the busy world behind. Book your Mackinac Island sailing charter today and experience the beauty of the Straits of Mackinac with Windy Escapes.
