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75-Minute Skyline Sail Aboard Tall Ship Windy: Celebrating Our 30th Season at Navy Pier! (Up to 33% Off)

600 E Grand Ave., Chicago

Tall Ship Windy

4.6
4,352 Groupon Ratings
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Highlights

New for 2026: Book your Skyline Sail now for trips running May 15 – June 26, 2026!

About This Deal

Highlights

  • 75-minute cruise with stunning views of the Chicago skyline and Lake Michigan

  • Sail aboard a historic tall ship for a truly unique, authentic experience

  • Onboard snacks and drinks for purchase, making your experience even more enjoyable

  • Boarding at Navy Pier for easy access to the sailing experience

  • Daily departures at 1pm, 3pm, 5pm, and 7pm from May 15 to June 26, 2026

  • Book your Skyline Sail now for trips running May 15 – June 26, 2026!

  • 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.

Tall Ship Windy 30th Anniversary

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.
What to expect image
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.

Plan Your Visit

  • Tour Schedule Sails daily at 1pm, 3pm, 5pm, and 7pm (May 15 – June 26, 2026)
  • Duration 1 Hour and 15 Minutes
  • Parking Available 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!

Fine Print

Promotional value expires Jun 26, 2026. 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. Not valid July 3rd, 4th, or 5th.

    • All purchases of this voucher are final and non-refundable.     Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Learn about Strike-Through Pricing and Savings

    About Tall Ship Windy

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    4.6
    4,352 Groupon Ratings
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