Tall Ship Adventures of Chicago

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Times shown are "cast-off" times. Please arrive 30-45 minutes early.

For all event descriptions


For specific sail, select the events name below.

Lakeside Architecture
Real Pirates
It's a Sailor's Life for Me!
Spirit Ships & Haunted Harbors
5:45p"Whale Watching" - Every Friday
Skyline Sail
Captain's Choice
9:15pm Wednesday Fireworks
9:15pm Saturday Fireworks

Sailing options:

Weddings and Wedding Parties

Field Trips


Educational Adventures


City of Chicago Resolution

Why choose Tall Ship Adventures of Chicago?

Tall Ship Adventures of Chicago offers sailing trips aboard several of Chicago's finest cruising sailboats. "Pianissimo", a 2011 Beneteau Oceanis 50 or Tall Ship Windy.

Your owners are not transient or seasonal employees of the company. Karen Randall and Capt. Bruce Randall are the owners of "Pianissimo" and Lakeshore Sail Charters, and also Tall Ship Windy, Tall Ship Adventures of Chicago, bring years of experience and knowledge of the Chicago cityscape and lakefront.

The personal touch of Tall Ship Adventures of Chicago continues with custom options. You may wish to have us provision, prepare your picnic, BBQ, or hors d'oeuvres and cocktails. For those who like to sail more frequently, but don't want to be locked into a time-share arrangement, generous discounts will be available for multiple date booking.

If you have a group larger then six (6) but still want to enjoy a lively sailing experience, Tall Ship Adventures of Chicago can offer you the option of a sailing trip aboard the Tall Ship Windy