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Tall Ship Windy

Discover Chicago’s Unique Sailing Excursions aboard the City’s Official Flagship

Explore Lake Michigan, on our Daily Sailing Tours

Choose us for your next special occasion or corporate event.
We offer private sailing charters

Welcome Aboard Tall Ship Windy

Tall Ship Windy, sailing from Chicago’s Navy Pier, brings you exciting sailing boat tours that are educational, creative and inspiring. From our daily skyline sails, to our Monday night concert sails to exciting Fireworks sails, enjoying the beautiful lighted skyline, there is something for everyone! Enjoy the Chicago skyline with us, as you sail on our tall ship!

For large groups joining a public sail (over 20) and private sailing charters, email us at tallshipwindy@lakeshoresail.com or call us at (872) 340-8400.

Illustration of fireworks

Tall Ship Windy
offers the most spectacular Chicago fireworks cruises during the summer.

Illustration of pirate hook

Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan.

Illustration of sailing ship

Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy.

Illustration of Chicago skyline

There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy.

Tall Ship Windy Chicago Sailing Reviews

A fantastic cruise! Windy City Boat Tours

We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!

– Deb R., Tripadvisor
Great way to end the summer Architectural Tour Chicago

We went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.

– Ron F., Tripadvisor
Always a good time Chicago Skyline Cruise

I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.

– Daniel C., Tripadvisor
Incredible experience Architectural Tour Chicago

If you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!

– Tina B., Tripadvisor
A sailing we will go! Navy Pier Boat Tour Chicago

Had a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!

– Cathy B., Tripadvisor
Sunset over the city Chicago Sunset Tour

Best view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.

– Lance B., Tripadvisor
Most fun tour in Chicago Navy Pier Boat Tour Chicago

The most fun tour we’ve had of Chicago. The crew is fantastic and the tour guide is hilarious. His sense of humor really sets this tour apart from the rest, while still offering interesting insights on the city’s unique skyline. Loved it.

– Nevillethehero., Tripadvisor
Best view of Chicago at sunset Chicago Sunset Tour

Loved our sail! I love sunsets and this in my opinion was the best way to experience the Chicago skyline. When I return I’d love to do another tour!

– Mallory R., Tripadvisor
Flawless perfection Boat Excursions Chicago

Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later.

– Roger H., Tripadvisor
Great sail on the Tall Ship Windy! Architectural Tour Chicago

The Tall Ship Windy is a must thing to do at Navy Pier. Very friendly and funny staff and always a good time, with beautiful views of the city of Chicago.

– Wekclk, Tripadvisor
Relaxing & amusing adventure! Navy Pier Boat Tour Chicago

My husband and I just did the "Pirate and Maritime Stories" tour with Tall Ship Windy and it was fabulous. A lovely cruise around the Navy Pier, while hearing some fascinating pirate history about Chicago. We highly recommend this experience for any age!

– Vacation22262481341, Tripadvisor
Chicago lifer and I loved it! Windy City Boat Tours

I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it! It was a gorgeous summer late afternoon and the city was just sparkling. I loved having a new view of the city. Crew excellent. My nephew helped hoist a sail. Narrator very entertaining and informative. I thought the price was great for the experience.

– Gwen S., Tripadvisor
Chicago from the water - worth every dime! Chicago Fireworks Cruise

What a great experience! Beautiful and ever-changing views of the night skyline from the lake. When they hoisted the sails and turned off the motor, it was so peaceful. The incredible fireworks were the perfect ending to this cruise. Highly suggest!!

– Venture30526260437, Tripadvisor