Sailing Adventures Aboard Windy

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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

Sailing Adventures Aboard Windy

Each day of our daily and weekly sailing schedule is unique, with every trip dependent on the direction of the wind. No two tours are alike. Each sail also has a tour theme led by our enthusiastic crew-educators! Our tall ship crew are multi-talented individuals, many of whom have experience in the study of history, maritime lore, the arts, music, and theatre- ready to bring their experience to enhance your enjoyment aboard Windy! You can simply relax on deck in quiet, or gather around for storytelling and hands-on fun! On any given day, you may find one or more of these sailing themes occurring during our famous Chicago Skyline day sails...

**Sailor's Paradise **Rum Runners **Real Pirates
**"Arrghitecture" Cruise **Guardian of the Harbor **Spirit Ships
**Sails Daily on the Tall Ship Windy
Expedition Sails 2.5 HOURS Moonlight Sails Sea Shanty
Fireworks Sail Blue Frontiers The Sailor and the Sea

Daily Featured Sails

Sailor's Paradise- The Life of Tall Ship Sailor - What did it take to survive and thrive out here in the Great Lakes as a sailor? It was a wild life of adventure! Great Lakes sailors knew how to build a life for themselves, independent and courageous, they turned these waters into a "Sailor's Paradise" Come find out why..

    What were the differences between the saltwater and the inland sea sailors? You'll soon know!
    Hear a lively tune or a traditional story!
    Learn the difference between a not and a knot in hands-on techniques you can use at home!
    See if traditional navigational technology can compete with modern computer in the chip log experiment!
It's not just a Sailor's Paradise, it might be yours too!

Real Pirates of The Inland Seas, A SPECIAL EVENT SAIL, will take you through the misty curtains of time to prove that not only is our great country founded on piracy with some of our forefathers as real pirates, but some of the most exciting and incredible tales of true piracy happened right outside of your front door - right here on these magnificent inland seas.

    But were all pirates "Bad Guys"? Where did the life of piracy originate? The answers may surprise you!
    Come along today and hear stories from 1600's to the 1960's of Great Lakes Piracy, tales from the Golden Age of Piracy all the way to its Twilight and we may just have to engage the enemy as we "privateers" defend our beautiful Chicago coastline!

Windy's "The Sailor and the Sea" Sail - The Ecologically Aware Tall Ship Sail - It's Sailing! It's Science! It's Adventure!
Don't get bogged down in the scientific doubletalk and fad advertising, -- Being Green is simple! . Here on the Tall Ship Windy we know that it could be as simple as just picking the right cruise! We use 80% less fuel then any other boat on the pier. Going green never was easier.

Our story tellers will take you on an incredible journey from through these waters and the world of environmental science...

Sailors have always been into conservation out of necessity, come find out why!
    Do a Hands-on science experiment!
    Play with the newest technology in alternate energy, it might surprise you!
    Hear about sea monsters that roam the deep! Perhaps even see them with your own eyes!

Blue Frontiers - A Chicago Maritime History Sail - Live and learn the Adventures of the Great Lakes Heroes and Heroines! Experience for yourself the inspiration of the these incredible waters.

Through storytelling and hands- on- sailing you will step back in time to the days where the Great Lakes were every bit as uncharted as distant space!

See it through their eyes...
    Could you explore three thousand miles of water in just a canoe? They did.
    Do you have what it takes to survive the isolation of lighthouse keeping? He did.
    Could you risk life and limb in a harrowing rescue attempt to save the lives of an entire ship? She did.

Come live the adventure, on The Blue Frontier Cruise.

"Aaarghitecture" Cruise! - Surely , this will be the most unusual architechture cruise you will ever experience! A Whimsical interpretation of our fair city's historical roots and maritime traditions which included a little-known legacy of Piracy on the Great Lakes! Journey back in time for some surprising stories!

Guardian of the Harbor - Our Chicago Harbor LIght House Sail... Chicago's Harbor Light is iconic! Hear its story as well as delight in stories of adventure, bravery, tragedy and triumph of Lake Michigan's Keepers of the Light.
•See the Harbor Light up close!
•Explore the science and wonder of the mythic fersnal lense!
•Hear traditional Light house Poetry and Songs

Rum Runners Chicago is known around the world for it's great food, amazing music and of course being the city of flappers and gangsters in the Roaring 30's. Using ships just like the Windy, hardened criminals and citizens turned crooks smuggled booze to the "dry" city of Chicago.
How did they get liquor into Chicago beneath the law's nose?
Who really ran this town, Capone, O'Bannion, or Captain Streeter?
Touch artifacts and replicas from this thrilling age.
Would you make it as a rum runner? Take our live quiz and find out!
It was a thrilling time in our history and a thrilling time on the Windy!

Spirit Ships and Haunted Harbors (September and October), A SPECIAL EVENT SAIL, A rousing sail and story telling adventure that peers into the dark waters of Great Lakes ghost ships and darker deeds of souls that sailed its shorelines. Written and performed by area historian, playwright, and storyteller Orion Couling; the WINDY invites you to sail through the misty curtains of time to hear stories that uncover mystery, history, legend and lore of our Sprit Ships and Haunted Harbors.

Other Sailing Events on Windy...

Windy's Fireworks Sail, A SPECIAL EVENT SAIL, - Our rousing adventure, on Wednesday nights and Saturdays, when you will be treated to Navy Pier's spectacular starlit Fireworks display, from the "best seat in the house" – sailing across the brilliantly lit skyline! Have a cool house specialty or a glass of wine from our bar* and relax to enjoy the show!

Sea Shanty Sails ♫ - Sea shanties (singular "shanty", also spelled "chantey"; derived from the French word "chanter", 'to sing') were shipboard working songs. Some speculate that shanties may have been sung as early as the 15th century. Shanties coordinated the movements of the sailors as they toiled at repetitive tasks. They also served a social purpose: they relieved boredom, and lightened the burden of hard work, of which there was no shortage on long sea voyages. You'll hear (and sing with us) a sampling of these legendary tunes.♫

Moonlight Sails - Our late evening peaceful sail under the stars! What better way to end the evening but with a nightcap aboard our majestic ship sailing across the amber-lit brilliance of the city skyline! Check the sunset times.

Expedition Sails -

New in 2011! On Friday afternoons, join the Captain and Crew of Windy for a long coastline sail of 2 1/2 hours and learn more about Tall Ship Sailing and Chicago's Cityscape and History!