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Tall Ship Windy
Chicago Sailing Tours

Celebrating 30 years on Lake Michigan, Tall Ship Windy invites guests to enjoy skyline sails, fireworks cruises, special event sails, group outings, and private charters from Navy Pier.

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Choose Your Chicago Sailing Experience

Explore Lake Michigan aboard Tall Ship Windy with public sailing tours, special event sails, and private charter options from Navy Pier. Whether you are looking for Chicago skyline views, Navy Pier fireworks, a unique boat tour, or one of the most memorable things to do in Chicago this weekend, Windy offers a sailing experience for every kind of guest.

Chicago Skyline Sail
Take in the Chicago skyline from Lake Michigan aboard a 148-foot, four-masted schooner. This public sail is a great option for families, couples, locals, and visitors looking for a unique alternative to a standard Chicago boat tour.
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Chicago Fireworks Cruise
Watch the Navy Pier fireworks from the water during one of Chicago’s most memorable evening experiences. This sail is ideal for guests searching for Chicago fireworks, firework shows near Navy Pier, or a special night out on Lake Michigan.
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Special Event Sails
From live music sails to seasonal events and Chicago Air and Water Show experiences, Tall Ship Windy offers special sails throughout the season. Check upcoming dates to find the right sail for your visit.
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Why Sail with Tall Ship Windy?

There are plenty of boat tours in Chicago, but Tall Ship Windy offers something different. Instead of a typical motorized sightseeing cruise, guests can step aboard a traditional tall ship and enjoy the lakefront from an open-air deck.

Guests choose Tall Ship Windy for:

  • Beautiful views of the Chicago skyline and Lake Michigan.
  • A convenient departure location at Navy Pier.
  • A unique sailing experience aboard Chicago’s Official Tall Ship.
  • Public sails, fireworks cruises, live music sails, group outings, and private charters.
  • A relaxed, photo-friendly way to enjoy the city from the water.

Planning a Group Sail or Private Event?

Make your next outing unforgettable aboard Tall Ship Windy. Our group sails and private charters are ideal for corporate events, school groups, church outings, weddings, family celebrations, reunions, and private parties.

Whether you are planning for a small group or a full private charter, our team can help you choose the right sailing experience.

 

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Popular Sails from Navy Pier

Chicago Fireworks Cruise
A public Lake Michigan sail with skyline views, fresh air, and a relaxed experience aboard Tall Ship Windy.
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Live Music Sails
An evening sail with views of the Navy Pier fireworks and the Chicago skyline from the water.
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Air and Water Show Sails
Experience one of Chicago’s biggest lakefront events from the deck of Tall Ship Windy during select Air and Water Show dates.
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Group Sails
Plan a group outing, field trip, company event, or celebration aboard Chicago’s Official Tall Ship.
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Loved your time aboard Tall Ship Windy? Reviews help future guests find us when they are looking for Chicago boat tours, Navy Pier sails, skyline cruises, and unique things to do in Chicago.

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Testimonials

What Guests Love About Tall Ship Windy

Guests love sailing with Tall Ship Windy for the skyline views, friendly crew, unique tall ship setting, and memorable Lake Michigan experience. Whether you are visiting Chicago for the first time or rediscovering the city as a local, Windy offers a different way to enjoy the lakefront.

Sunset over the city
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.
WekclkTripadvisor
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!
Vacation22262481341Tripadvisor
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!!
Venture30526260437Tripadvisor
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.STripadvisor
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 BTripadvisor
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