Discover the Magic of Mackinac Sailing
Experience breathtaking views and custom journeys aboard our classic sailing yacht on Mackinac Island.
Our Story
Windy Escapes is more than just a sailing charter; it’s a dream come true, combining a love for sailing with the tranquility of the Great Lakes.
Join us for unforgettable moments on the water with a dedicated crew.
Explore Our Sailing Options
Private Sails
Experience the thrill of a private sail aboard our classic 1966 Columbia 50. Perfect for up to 6 guests, this intimate cruise features non-alcoholic beverages, concierge services, and stunning views of Mackinac Island. Create unforgettable memories on the water.
Custom Charters
Design your own sailing experience with our custom charters. Whether it’s a romantic escape, family gathering, or special occasion, we can adjust the duration and port of call to meet your unique needs, ensuring a personalized adventure on Mackinac’s waters.
Sunset Cruises
Join us for a magical sunset cruise and witness the sky painted in vibrant colors as the sun dips below the horizon. Enjoy the gentle breezes and serene waters while making memories that will last a lifetime. Perfect for families, couples, or friends.
Veteran Specials
As a veteran-owned business, we honor those who serve with exclusive discounts and personalized offers for active-duty military and veterans. Enjoy tailored booking options to experience the beauty of sailing while receiving the recognition and respect you deserve.
Our Memorable Journeys and Client Experiences
Intimate Private Sails
Spectacular Sunset Cruises
Tailored Custom Journeys
Embark on Your Sailing Adventure Today!
Why Choose Windy Escapes
Veteran Owned
As a veteran-operated business, we honor those who serve, providing exclusive offers for military personnel.
Customizable Charters
Tailor your sailing journey to your preferences, creating unique experiences that suit your desires.
Experienced Crew
Sail with our seasoned captain and first mate, ensuring safety and enjoyment throughout your journey.
Best way to see Mackinac Island and surrounding islands from the water. Captain Mark and First Mate Kai are very knowledgeable and fun to spend time with. It was one of the best things my family did on Mackinac.
Seth McDowell
Captain Mark was super! Tried his best to assure us a great sail in nice weather. Our “birthday boy” loved taking the helm (at 84). Highly recommend this cruise.
David Frost
Wonderful sailboat tour! Mark and his crew were great sailors and gracious hosts – would definitely recommend to anyone looking for a getaway from the crowds to escape to the beautiful waters.
Aaron Hirshberg
Ready for Your Own Sailing Adventure?
Contact us today to customize your unforgettable sailing experience on Mackinac Island.