Tall Ship Adventures of Chicago

Near North Side

2302 Ratings

Value Discount You Save
$587 66% $388
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In a Nutshell

Up to three couples gather on deck of graceful sloop-rig sailboat for personalized day tours & shoreline fireworks shows

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. 72hr cancellation notice or fee up to Groupon price may apply. Reservations available starting 5/1/12. Subject to availability. Must be 12 or older. Must sign waiver; consent by guardian required if younger than 18. Subject to weather. Not valid during weekend of Chicago Air & Water Show. Not valid 8/17 - 8/19. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

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.

$199 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 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.

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.

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

2302 Ratings

It was a great trip.
Chris H. · November 2, 2016
Had an awesome time on this ship ride. Staff were friendly and funny. Ship was just gorgeous! I would highly recommend this! Loved it!
Sandra M. · November 2, 2016
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
Merchant Location Map
  1. 1

    Near North Side

    111 N. Lake Shore Drive

    Dock B, Slip 7

    Chicago, Illinois 60611

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