View of the Round Island Passage Lighthouse in the foreground, with the shoreline of Mackinac Island's business district visible in the background under a cloudy sky. This is the location where all sailing charters will begin.

Set Sail on Mackinac’s Only Sailing Charters

Private 2-hour sails, sunset cruises, and custom journeys aboard a classic 1966 Columbia 50.

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Plan a Custom Trip

Your Windy Escape Awaits

At Windy Escapes, we specialize in exceptional sailing charters that allow you to explore the breathtaking Mackinac Island shoreline.

Don’t miss out on the adventure of a lifetime! Book your charters today and create unforgettable memories with friends and family!

A classic red-hulled sailboat named Stampede sails on open water under a cloudy sky. The vessel features white sails and a sleek design, with a crew visible near the stern and is available for sailing charters. The water is slightly choppy, and the horizon is visible in the background.
The sailboat Stampede glides through the channel in South Haven, Michigan, with calm water beneath and a breakwater lined with rocks and lighthouse structures in the background.

At Windy Escapes, we understand that every group is unique. Our custom charter options allow you to tailor your sailing experience to fit your needs and desires! Connect with us to plan yours.

Choose Your Adventure

2-Hour Private Cruise

Max 6 guests.

Non-alcoholic beverages provided.

Concierge services for other food and drink included.

Prices start at $400.

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Customized for You Cruise

Up to 6 guests but may be fewer depending on request.

Variable duration.

Variable ports of call.

Prices vary.

Custom Inquiry

Our Special Guests

Prefer to talk to a real person? Give us a call or text. If we are out on a cruise, we will call you back as soon as we are able. 906-298-1744

What to Expect Onboard

Calm, scenic routes with views of Mackinac’s historic coastline

A classic 50-foot sailing yacht with a comfortable deck

Guests are welcome to relax or help sail

Friendly captain and crew

Bring your own snacks and drinks (or talk to us about concierge service)

Stampede Info Page – Coming Soon
The sailboat Stampede sails up the South Haven channel, flanked by breakwalls and a red lighthouse, with passengers visible on deck enjoying the ride under a partly cloudy sky.
The sailboat sailing at sunset. The sky is tinged with orange and pink hues, and the calm water mirrors the tranquil scene.
A vibrant spinnaker sail billows in the wind against a clear sky, capturing the power and grace of the sailboat A sailboat as it moves under full sail. Only the sails are visible, highlighting the colorful patterns and motion.

As a veteran-owned and operated business, we proudly honor those who serve and have served. Veterans and active-duty military hold a special place with us—reach out to learn about exclusive discounts, personalized offers, and flexible booking options.

Are you looking for Adventures with Vagari? Select the button to visit svvagari.com and learn more about the adventures Mark, Christy, and their friends and family have aboard Vagari, a Whitby 45.

Visit Adventures with Vagari