Tall Ship Windy - Sail Training details page

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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


Ahoy! Join us for an exciting educational adventure aboard the Tall Ship Windy! Great Lakes history and maritime tradition come alive from the decks of our floating classroom with Windy's Tall Ship Discovery Sail for sail training. This unique, hands-on learning experience is a great way to enjoy physics, ecology, history, and storytelling while taking an active part in sailing the vessel. Call us at 312.451.2700 for pricing and availability!


Our curriculum is customizable and appropriate for novice sailors of all ages. Students "muster" to participate for a total of three learning stations. We provide two of them:

  1. Harnessing the Wind: The "physics" of how a sailing ship sails. With wind as a free energy source, the greatest use of it has been by sailing ships. This module explains how a sailing ship "works", how it can sail against the wind and change direction, and familiarizes the student with the terms associated with sailing.
  2. The Language and Life of a Sailor: This section is designed to teach the student nautical terms and names for the vessel parts and provide hands-on exploration of the tools, trinkets, and nomenclature of a sailor from the 1880s to the present.
  3. And the third is up to you! Choose from one of those listed below!

Windy Third Station Options

History and Lore: The History and lore of tall ship sailing from our ancestral origins to present day - Includes the role of Tall Ships in World Exploration, Commerce, Warfare, and finally, leisure. It's a sailor's life for Me!

Real Pirates of the Inland Seas: The story of actual piracy on the Great Lakes and its impact on the development of our region. This module examines the controversial morality and mystique of the pirating life, dispelling myth, and portraying the historical realities.

Tall Ships and Ecology: Sailing vessels harness the wind, a natural energy source, and serve as platforms for research on climate change, water, and environmental conservation, and the development of alternative energies. Explore this, along with a hands-on experiment right there on Windy!

Marlinespike Seamanship: The Skills of the Traditional sailor: Involves fun, hands-on exercises that will teach students about the tools and trade of the Sailor: historical uses, rope work, block and tackle systems, rigging, and the function of sailors' knots and how to tie them.

Strong women of the Lakes: They were lighthouse keepers. They were sailors and explorers. They were rum runners. They were the women of the Great Lakes. Hear "herstory" rather than "history" on this exciting girl-empowered station.

Scout small craft badges: Did you know we can pack the small craft badge/patch into one lesson plan? Covering the material that you need to surpass the Scouts' expectations for your knowledge about basic water safety. Please note that we offer the actual patch/badge of our ship to your youth at a small additional cost!

Schedule & Pricing

With start times of:
10 or 10:30am, 12 or 12:30 weekdays
10 or 10:30am weekends - If available.

Group Size:
Best suited for groups of 50-130

Weekdays - $10/person with a $500 minimum
Weekends - $15/person with a $750 minimum

Windy reserves the right to combine groups or individuals based on space. Private educational sails are also available, for an additional cost

To book your adventure or for more information, call 312.451.2700 today!