Tall Ship Adventures of Chicago

Near North Side

2296 Ratings

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$30 50% $15
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In a Nutshell

148-foot four-masted schooner ferries up to 150 guests around Lake Michigan as they learn about sailing & Chicago history

The Fine Print

Promotional value expires Jun 20, 2012. Amount paid never expires. Subject to availability. Same-day walk-up reservations only. No advance, internet, or phone reservations. Valid only for adult tickets. Not valid during festivals or special events. 9% tax and gratuity not included and payable at time of redemption. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Before the invention of sails, armadas relied on outmoded ship designs such as the Vikings' 30-man paddleboat and the languorous, elegant war gondola. Sail on a ship as swift as the wind with today's Groupon: for $15, you get an adult ticket to a cruise on the tall ship Windy from Tall Ship Adventures of Chicago (up to a $30 value). Discounted tickets based on age are available, so be sure to check rates.

Honored by former mayor Richard M. Daley as the flagship of the city of Chicago, Windy spirits up to 150 sightseeing sailors about Lake Michigan on its 148-foot four-masted back. The schooner's suite of themed cruises, 60–75 minutes long, give customers the opportunity to learn about historical topics such as Great Lakes piracy, Prohibition-era bootlegging, and the Chicago Harbor Lighthouse, all while taking in views of the city skyline or searching the heavens for a sign from your patron astronaut. Interested passengers can help with sail raising and aid the experienced crew with other shipboard activities, learning how to crew masted ships in the process. Today's deal can also be applied toward more costly outings, such as the Wednesday-night fireworks cruises and the 2.5-hour Friday cruises, which help would-be sailors acquire sea legs and fashionable sea hair teeming with plankton and anemones.

Tall Ship Windy

The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.

Customer Reviews

2296 Ratings

So much fun! Adventure of the summer!! Very, very pleasant staff and knowledgeable!!! The Captain was amazing and super nice!!!!
Jane B. · October 14, 2016
We took the 10.30 am Architectural Sail in second week of September. The weather was marvellous! The image of The beautiful skyline of Chicago with clear blue sky as a backdrop is still so fresh in our minds! My husband loved it too. The crew was so entertaining. They dont let you get bored. I was sad that 75 mins were over so soon. They also let you pull up the sails! Austin as a guide was more like an energetic story teller😃. Tall ship Windy is gorgeous! Had a great experience. Thank you Captain for navigating🤓Ahoy! We will be back soon!
Srijita S. · September 25, 2016
They were so knowledgeable and nice! Had a great time :)
Melody R. · September 20, 2016
Merchant Location Map
  1. 1

    Near North Side

    600 E Grand Ave.

    Chicago, Illinois 60611


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