$229 for a 2.5-Hour Semiprivate Sail for Two from Tall Ship Adventures of Chicago (Up to $587.50 Value)

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Up to 61% Off

Customer Reviews

2,662 Ratings

Great adventure and a good host
Jason G. · 3 days ago
Our experience was wonderful---kind employees, very experienced, and told us a lot about the area were seeing--the boat was clean, plenty of room--great experience ! ( even with a 3 yr old ! )
KRIS S. · October 1, 2017
Such a fun and informative tour! The BEST
Linda W. · September 29, 2017

What You'll Get


Sailors get their name from the sails they use to capture the wind, which could previously only be caught by setting a pile of autumn leaves as bait. Experience wind hunting in action with this Groupon.

$229 for 2.5-Hour Semiprivate Sail for Two (Up to $587.50 Value)

Guided by captain Bruce Randall and Captain Jim, up to three couples glide near the lake's coast aboard the Pianissimo, a 2011 Beneteau Oceanis 50 sloop-rig sailboat, while sipping and noshing on food and beverages brought from home. Crews personalize each excursion to the interests of their passengers, but can chart a course for special events such as 8 p.m. shoreline fireworks shows. Tours set sail at 6 p.m. and 9 p.m. Monday through Friday, or 9 a.m. and noon on Saturday and Sunday.

Tall Ship Adventures of Chicago

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 and the rumrunners who filled the city's speakeasies as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard the Windy, one of Tall Ship Adventures’ three ships helmed by U.S. Coast Guard-certified captains and crews. These nostalgic vessels are used to educate visitors on the lake's maritime traditions and explore coastal waters. Though the Windy plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles, captains also conduct day, evening, and night sails aboard the Pianissimo. 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.

The Fine Print


Promotional value expires Sep 1, 2012. Amount paid never expires. Limit 1 per person, may buy 2 additional as gifts. Limit 3 per visit. Reservation required 10 days in advance; subject to availability. 5% processing fee may apply for cancellations; less than 2wk notice may incur fee up to 1/2 of Groupon price and less than 72hr notice may incur fee up to Groupon price. Must be 12 or older. Must sign waiver or have guardian sign waiver if under 18. Not valid for Air & Water Show weekend. Subject to weather. Valid for Mon-Fri 5pm or 8pm sails and Sat-Sun 8am or 11am sails. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

About 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 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.

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