Skip to primary navigation Skip to content Skip to footer

Tall Ship Windy

The Official Flagship Of The City Of Chicago
Chicago Skyline Tours & Boat Excursions
Sailing On Lake Michigan From Navy Pier

View All Sails
MOST POPULAR!

Chicago Skyline Sail

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

Hour Glass 75 Minutes | Starting at $39

BOOK NOW!
a large ship in a body of water with a city in the background
From $50 per Person
  • 90 Minutes

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy!

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

Book Now
Learn More
  • VIP Event, 1 Night Only
From $89 per Person
  • One Day Only - VIP Event - 1.5 Hours

4th of July Independence Celebration Sail! Aboard Chicago's Official Tall Ship Windy!

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town!

Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July 4th, but officially this has not been announced. Chicago’s Fourth of July celebration is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, is truly a VIP event. This event sells-out early.

Book Now
Learn More
From $59 per Person
  • 2 Hours

Monday Night Blues Summer Concert Series

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago at sunset from the waters of Lake Michigan, accompanied by the sweet sounds of the blues.

Book Now
Learn More
  • Frequently Sells Out
From $49 per Person
  • 75 Minutes

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

Book Now
Learn More
  • Every night at 5pm!
From $39 per Person
  • 75 Minutes

Happy Arr-our Chicago Architecture and Skyline Sail

Enjoy happy hour drink specials onboard this Navy Pier Boat Tour every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration and an Architectural Tour of Chicago from the water.

Book Now
Learn More

Explore Chicago Sailing Special Events

Chicago Fireworks Cruises

Special Event Sails

Welcome Aboard Tall Ship Windy

Tall Ship Windy, sailing from Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative and inspiring. From our daily storytelling adventures and field trips for students to our concert sails to lively Chicago Architectural Tours, there is something for everyone. Enjoy the Chicago skyline as you sail on our tall ship!

For group boat excursions and private sailing charters, email us at tickets@tallshipwindy.com or call us at (312) 451-2700.

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.

View All Sails
Learn More

Choose Tall Ship Windy For Your Special Event

Private Sailing Charters Learn More

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