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Proposal Charter

An engagement proposal is something that both of you will remember for the rest of your life. So, what better way to create this fantastic memory than sailing on a private proposal charter from the comfort of one of our exquisite yachts with the beautiful Chicago skyline as your backdrop?

Your proposal charter with Windy City Sailing can occur under the colorful canopy of the bursting fireworks.  Or, you could choose a more intimate setting on a relaxing morning, afternoon, or evening excursion.  Either way, it will be a memorable occasion.

Marriage Proposal Charter with Windy City Sailing

What do we need to bring on the sailing charter?

We provide our guests with all the amenities needed to make their night a night to remember. On all of our excursions, guests will be provided with bathrooms, comfortable seating areas, bottled water, ice, and a cooler that can store any of the treats you decide to bring with you on your journey. Feel free to bring along your own music to enhance the viewing experience with surround speakers on the topside. Our experienced crew and captain will handle getting you and your party to the show and you don’t have to worry about anything except for having a good time.

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WINDY CITY SAILING HAS PROUDLY BEEN OFFERING EXCEPTIONAL SERVICE FOR TWO DECADES, AND WE HAVE SATISFIED RETURNING CUSTOMERS TO PROVE IT!

Frequently Asked Sailing Questions

About Our Captains

Our US Coast Guard licensed captains will sail you along Chicago’s skyline in style. Some of our guests enjoy hearing interesting facts about Lake Michigan and our city’s history. But others prefer to enjoy the intimate setting without interruption. Either way, our captain and crew are here to cater to your wishes and ensure that you enjoy every moment of your anniversary charter. 

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