Each day our 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...All of our regular scheduled sails are 75 minutes in length.
Arrrchitecture Cruise
EXPLORES CHICAGO'S SHORE through history! Study the skyline from a beautiful lakefront vantage point to learn about the people, plans, and persistence that shaped Chicago’s most famous sights. From our maritime roots to our distant hopes, our docents will delight you with interesting facts, unique stories, and a healthy dose of comedy.
Offered: May – October
Living History
Fun for All
Real Pirates of the Inland Seas
TRUE STORIES OF PIRACY on the Great Lakes! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas.
Offered: May – October
Hands on History
Great for Families
Sailor’s Paradise: The Life of a Tall Ship Sailor
What did it take to SURVIVE AND THRIVE out here on the Great Lakes as a sailor? Discover the danger and delight of life on the open water and find out how these hearty folk turned the Great Lakes into the ultimate Sailor’s Paradise.
Offered: May – October
Hands on History
Fun for All
Chicago Lighthouse Sail: Guardians of the Harbor
GET UP CLOSE to the iconic Chicago Harbor Light! Across the Great Lakes, lighthouses and their keepers have always stood tall as beacons of hope, strength, and innovation. Come take part in their unique legacy.
Offered: May – October
Living History
Rum Runners
Swing into ROARING 30’s CHICAGO, where gangsters ruled schooners and speakeasies alike! Uncover the amazing truth behind these cunning criminals and their outrageous plots to smuggle booze into the “dry” city of Chicago.
Offered: May – October
Living History
Adult Themed
Spirit Ships and Haunted Harbors
This STIRRING AND SPOOKY storytelling adventure peers into the dark waters of Great Lakes ghost ships and the darker deeds of souls that sailed its shorelines. As night falls and the seas grow dim, journey through the misty curtains of time to uncover the mystery, history, legend, and lore of our Spirit Ships and Haunted Harbors.
Offered: May – October
Living History
Adult Themed
Fireworks Cruise and Sea Shanties!
A SPECIAL EVENT SAIL! Relax and enjoy Navy Pier’s spectacular fireworks display from the best seat in town. Then, get your history fix with a rousing rendition of traditional shipboard working songs against the backdrop of the brilliantly lit Chicago skyline. It’s the best of both worlds!
Offered: Saturday Nights; June – October
Family Friendly
Music
Fireworks Cruise and Spirit Ships!
A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago skyline. Then, join our storytellers on the main deck, if you dare. As night falls and the seas grow dim, journey through the misty curtains of time to uncover the mystery, history, legend, and lore of our Spirit Ships and Haunted Harbors.
Offered: Wednesday Nights; May – October
Living History
Family Friendly – Ghost Stories Offered on Main Deck