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Tall Ship Windy

The Official Flagship of the City of Chicago
Chicago Skyline Sails & Tours

Anchor View All Sails

Sail in Florida and the Virgin Islands!

Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.

If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.

Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.

No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.

Paradise Adventures Catamarans and Watersports

Panama City Beach, Florida

Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!

  • Experience inflatable fun on a Privateer Adventure Tour
  • Snorkel and explore Shell Island
  • Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
  • Book a private charter on a catamaran, sailboat, powerboat or pontoon boat

Learn more about Paradise Adventures

Charter Smarter

Virgin Islands

Explore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!

  • Each week-long adventure includes a professional captain, a skilled chef and all meals and drinks
  • Take advantage of all your catamaran’s amenities, water toys and land-based activities in paradise
  • Bring your family or friends and create memories that will last a lifetime

Learn more about Charter Smarter

Seas the Day Charters USVI

US and British Virgin Islands

Enjoy a full or a half-day adventure with Seas the Day Charters USVI!

  • Luxury sailing excursions & fast powerboat adventures
  • Private & semi-private charters available
  • Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
  • Explore the US Virgin Islands or the British Virgin Islands

Learn more about Seas the Day Charters USVI


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

Hour Glass 75 Minutes | Starting at $39

From $55 per Person

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.

From $99 $79 per Person

Chicago’s famous 2 hour Pirates Pub Sail departs every Friday night at 8:45pm aboard Tall Ship Windy at Navy Pier. Yes, this is Chicago’s Famous and Only Floating Pirates Pub!

Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan.  Chicago’s famous Pirates Pub Sail is an event that should not be missed.

Choose a Sailing Category

Welcome Aboard Tall Ship Windy

The Tall Ship Windy, located on 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, there is something for everyone. Come enjoy the Chicago skyline as you sail on our tall ship!

For groups or charters, email us at [email protected] or call us at: (312) 451-2700

Illustration of fireworks

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

Illustration of pirate hook

Our sails 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 experience on Tall Ship Windy.

Illustration of Chicago skyline

There is simply no better way to experience Chicago’s world-famous skyline than on the Tall Ship Windy.

Have a special event coming up?

Catch these five-star reviews from TripAdvisor!

Deb R profile photo
A fantastic cruise!

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
Ron F profile photo
Great way to end the summer

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
Daniel C profile photo
Always a good time

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
Tina B profile photo
Incredible Experience

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!

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

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