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.
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 home-brought food and beverages. 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.
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.
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