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Enjoy a wonderful day in the lap of luxury as you sail gracefully in the wide open waters of Lake Michigan on a private skippered sailing charter.
Sit back, relax and enjoy as your captain sails you and your party across Lake Michigan.
Chicago sailing conditions can be calm or exciting. Whether you are looking for a romantic sailing trip for 2 or a day on the water with 5 of your closest friends, your captain will do everything possible to suit your sail to your wishes.
Your stylish 39 foot luxury cruiser was designed for a balance of comfort and performance. Because of this design, the seating area in the cockpit is very large and there is a great deal of deck space. Able to sail in even the lightest of winds, as well as heavy conditions, this is the perfect ship for Lake Michigan pleasure sailing.
The sailboat is also equipped with hot and cold running water, a swim platform and swim shower, large retractable canopy and cockpit seat cushions. The interior boasts large bathrooms, beautiful teak and holly floors, and more than ample cold storage for all your food and drinks.
This is sure to be to an experience you and your friends will be talking about for a long time.
Fireworks Sail: Every Wednesday from Memorial Day through Labor Day, Navy Pier puts on fireworks displays that last about 10-15 minutes. Note: To book a sail at this time, there is a 4-hour charter minimum.
Free Exchanges
No Expiration Dates
Easy Returns
Essential Information
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Experience Provider Info
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Spectators
Weather Dependent
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Experience ID
Free Exchanges
No Expiration Dates
Easy Returns
Free Exchanges
No Expiration Dates
Easy Returns
May through October:
3 Hour Charter
Sunday through Friday - 4:00 PM
3.5 Hour Charter
Sunday through Friday -12:00 PM
4 Hour Fireworks Charter
Wednesdays - 7:30 PM
Pick the perfect experience gift or buy an egift card and let your recipient choose their own adventure.
After checking out, you can easily print or email your Experience Voucher. While delivery is instant, the memories will last a lifetime.
Your recipient can book their experience at their convenience either online or by calling us. And if they'd prefer to do another one, they can easily exchange it.
Our trusted vendors and passionate team will ensure that your recipient will be treated to the experience of a lifetime—making memories that will last for years to come.
Our experienced team takes the risk out of gift-giving with handpicked experiences that are guaranteed to delight. We only work with top-rated experience providers and offer flexible policies to make giving a great gift a no-brainer—no matter who you're shopping for.
Learn More »We offer 30-day returns or your recipient can easily exchange their gift for anything else in our marketplace, anytime—free of charge.
Our vouchers never expire, so your recipient can redeem them at their convenience.
No markups, no added fees. You'll pay the same price as buying directly from our experience providers, but with the flexibility of easy returns and exchanges.