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    Sip n' Sail Cruises

    4.9 (15 reviews)

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    Lily M.

    If you find yourself on Mackinac Island, I highly recommend Sip n' Sail Cruises. This was my first time and it was an unforgettable experience that left me in awe of the breathtaking views it was a very romantic evening. The highlight of the cruise was undoubtedly the stunning scenery as we sailed under the Mackinac Island Bridge during the golden hour. Great photo opportunities! The staff on board were exceptional in ensuring a memorable experience for everyone. They were organized and attentive, making sure guests were well taken care of throughout the journey. What impressed me the most was that I always had a drink in my hand. A hot tip though: The seats on the deck fill up quickly, and most passengers prefer not to sit inside. My partner and I discovered a hidden spot at the front of the boat that no one seemed to check, and we were able to snag a prime seating location. But even so, it was very crowded, not shoulder to shoulder but you were for sure bumping people. That is why I only gave it 4 stars, I wish they limited the number of people a bit more. While you can stand the entire time, having a spot to sit was nice for the 1.5-hour cruise.

    Jacque W.

    This is an ABSOLUTE MUST when planning your trip to Mackinac!! Molly is simply the best, most kind hostess!! We are from Texas and were told you didn't need to make reservations by someone at one of the hotels. It is best to have reservations. Molly made room for us!! It was one of the highlights of our 5 day trip to the island!! We loved every minute. The music was great. The whole experience was fabulous!! We would go again and again for sure and you are missing out if you do not incorporate this into your travels plans!!

    Photos from the tour
    Becky S.

    Must make this experience part of your Mackinac Island adventure! Take a break from the smell of horse poop and relax and enjoy a cruise with spectacular views. Laugh and drink with friends or get up and dance to the live music. Not a big fan of boats here, but the waters were calm, the music was great and the views were amazing! The fact that there was always land in sight helped with the fear of boats and maybe the open bar, too. The Captain kept the journey mild and relaxing, no boat racing here! Well worth the price! Don't pass up this experience!

    Up close and personal to Round Island lighthouse
    Walker V.

    Looking for a fresh take while on Mackinac Island? Why knot try the Sip n' Sail while you're on your Island Adventure! Departs twice daily in the summer around 4 and 8pm for a truly a moment to remember... Set sail for a sunset ride to the Mackinac Bridge with the fun loving crew of the Queen Mary the III. A regal vessel with an historic past celebrating their 5th season on the Straits of Mackinac. Captain and crew greet and welcome you aboard. There was a birthday party as well as a bachelorette party in tow. Special shout outs from the live musician who was rocking out Dave Matthews to John Cougar. Being from Scottsdale Arizona I enjoyed standing on the bow catching some Lake Michigan mist. Plenty of seating below deck and a few seats above. Get there early so you can get one of the captains chairs on the second level. Personally, I didn't sit down the entire trip, but then again I like going to the galley and refilling my cocktail at the well stocked bar. Beer, wine and liquor available. Marinated peaches in Grand Marnier, i i Captain!! You will not be disappointed in your mini adventure within the Mackinac Island experience. A truly unique experience off the shores of Mackinac Island that gives you something to talk about for the rest of your life. Thanks for the memories Captain V. You are an Island Treasure! -Walker

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    Review Highlights - Sip n' Sail Cruises

    . Not too mention, the sunset was beautiful, which they timed perfectly to be under the Mackinac Bridge to view

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    Windy Escapes - Stampede (a 1966 Columbia 50 painted red) with sails furled floating on open water. Tree lined land in the background.

    Windy Escapes

    (1 review)

    Sailing with Windy Escapes, aboard the Stampede, was a wonderfully enjoyable cruise…read more Captain Case and first mate (and son) Kai, both experienced sailors, were passionate about sharing their knowledge of Mackinac Island. Incredibly accommodating, they made sure we were comfortable and confident before leaving the marina, and ensured a welcoming atmosphere on board, giving us a safe and authentic smooth sailing experience, and making us feel at home. Captain Case's workmanship and care for his boat and crew were evident in all his actions. The postcard-worthy views of the island from the boat provided a mesmerizing backdrop of natural beauty that truly left me in awe. The weather was perfect, and the Lake Huron waters cool, clear, & clean. We loved every minute aboard Stampede and would definitely consider a repeat trip.

    From the owner: Set sail from Mackinac Island State Harbor aboard our stunning Columbia 50 sailboat for a private…read morecharter experience like no other. Operating daily from June 10 through the end of September, 9 AM to sunset, our sailing charters accommodate up to six passengers-perfect for couples, families, or small groups. In addition to standard excursions, we also offer custom charters tailored to your unique interest, whether it’s a romantic sunset sail, a special celebration, or a full-day adventure. Enjoy a personalized and professional sailing experience from one of Michigan’s most iconic destinations. Book your charter today at windyescape.com.

    Sip n' Sail Cruises - boatcharters - Updated August 2026

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