Famous Sites

Lakeside Architecture Sail

Explore Chicago's architectural majesty while sailing across our beautiful lakefront skyline. Learn about the people, plans, and persistence that shaped Chicago's most famous sights. From our historical maritime roots to modern science and technology, you will be delighted with interesting facts, unique stories, and a healthy dose of whimsy.

Saturday Night 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.
4th of July Fireworks!!

Fourth of July Fireworks

Treat yourself to Navy Pier’s spectacular Fourth of July 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.

Marshall Vente Jazz Cruise

Join Marshall and his band on an evening cruise aboard the Tall Ship Windy, as they sail across the memorable Chicago skyline, quietly under sail power, while he serenades the you with his own tropical jazz fusion of music, now is your chance to enjoy the limited event, and have memories that will last a lifetime.

Wednesday Night Fireworks Cruise

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!
Great for Families

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.

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 light grow dim, journey through the misty curtains of time to uncover the mystery, history, legend, and lore of Spirit Ships and Haunted Harbors.

A Sailor’s Life for Me!

What did it take to survive and thrive as a Tall Ship sailor? On this trip through time, hear the story of how Tall Ship sailors became sailors, where in the world they sailed, and what they did on these great ships! See and touch their tools of the trade, discover how they lived every day, and what made Tall Ship sailing on our Great Lakes, "Great"!

Educational Sail: Tall Ship Discovery Program

SHARE THE MARVEL of maritime heritage on the Great Lakes! History comes alive with an exciting educational adventure for curious minds of all ages. Join a local school or youth group, on their sail training mission, for hands-on sailing aboard Windy, and then muster for learning stations led by our crew-educators.
Will Return in September

Skyline Sail

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water.