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Highlights
Step aboard a vessel where history meets horizon. With towering masts and canvas sails overhead, Tall Ship Windy takes you on a ride that’s equal parts adventure and serenity. Conveniently located at Navy Pier, Tall Ship Windy is the first official Tall Ship Ambassador of the City of Chicago.
About This Deal
Highlights
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75-minute cruise with stunning views of the Chicago skyline and Lake Michigan
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Sail aboard a historic tall ship for a truly unique, authentic experience
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Onboard snacks and drinks for purchase, making your experience even more enjoyable
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Boarding at Navy Pier for easy access to the sailing experience
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Daily departures at 1pm, 3pm, 5pm, and 7pm from August 4 to September 28, 2025
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New for 2026: Book your Skyline Sail now for trips running May 15 – August 31, 2026!
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Perfect for Gifting: A unique and thoughtful gift for any occasion - give the experience of a relaxing sail on Lake Michigan, perfect for friends, family, or loved ones.
What To Expect
Whether you're seeking a tranquil day on the water or want to admire the stunning skyline from a unique vantage point, this 75-minute sail on Lake Michigan provides an unforgettable experience. As you glide across the water, you'll be treated to breathtaking views of the Chicago skyline while the gentle waves beneath you create a soothing escape from the city's hustle and bustle. Onboard, you can unwind with snacks and drinks, enhancing the peaceful atmosphere of your journey.
Departing daily from Navy Pier, the Tall Ship Windy allows you to experience Chicago’s beauty from a whole new perspective. With scheduled sailings at 1pm, 3pm, 5pm, and 7pm, there's a perfect time for everyone to embark on this relaxing adventure. Whether you're a local or a visitor, this sail offers a chance to connect with the city's charm in a calm, serene environment.
Planning ahead? You can already secure your spot for the 2026 season! For next year, Tall Ship Windy is offering the same unforgettable trips! Buy your 75-minute Skyline Sail now for departures running May 15 through August 31, 2026, and lock in your perfect summer experience early.
Plan Your Visit
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Tour Schedule Sails daily at 1pm, 3pm, 5pm, and 7pm (August 4 - September 28, 2025)
2026 Season: Daily Skyline Sails available May 15 - August 31, 2026 -
Duration1 Hour and 15 Minutes
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ParkingAvailable at Navy Pier; please arrive early to allow time for parking
How It Works
1. Grab the Deal
Buy your Groupon first!
2. Plan your Visit
Follow the link on your Groupon to select the date.
3. Redeem your Mobile Ticket
Enter your Groupon code at checkout.
4. Enjoy the Experience!
FAQs
What types of sails are available?
Tall Ship Windy offers various sailing experiences, including:
Chicago Skyline Sail
Fireworks Cruise
Monday Night Concert Series
4th of July Independence Sail
Air & Water Show Special Event
Each sail offers a unique experience, showcasing different aspects of Chicago's skyline and waterfront.
Are there any age restrictions?
The sails are suitable for guests of all ages. Children under 1 year old can sail for $10, while children aged 1–12 years have a reduced fare. Adults aged 13 and above are charged the full fare.
What amenities are available on board?
The Tall Ship Windy is equipped with three spacious decks, a grand salon, pressurized marine toilets, and a bar offering a selection of beverages and snacks. Guests can enjoy the scenic views while relaxing in comfort.
What should I bring with me?
We recommend bringing comfortable clothing, sunscreen, and a valid ID for any on-board purchases.
Is food and drink included with the ticket?
No, food and drinks are available for purchase on board, but they are not included in the price of the ticket.
Fine Print
Expiration varies. Amount paid never expires.
Booking: Online reservation required. May purchase multiple to accommodate your group size. Restrictions: Valid only for option purchased. Taxes not included and collected at time of booking. Trips sail rain or shine. It is up to the captain to decide whether to sail, postpone or cancel. Not valid for special events or specialty sails. All sales final.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.
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About Tall Ship Windy
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