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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. 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. Join us for a family-friendly fireworks cruise on the Chicago River!
Popular Sails
Sail into the night and embark on a two-hour party sail from Navy Pier; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This popular Chicago event is one you will not want to miss; it is unlike all other boat excursions in Chicago. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights on Lake Michigan. On Wednesday and Saturday evenings, you can take our Skyline Lake Tour and end your visit with a front-row view of the Navy Pier fireworks.
Chicago Skyline Sail
Group discount rates are available for parties of 20 or more aboard any of our river cruises. Summer Fireworks Wednesdays (9PM) & Saturdays (10PM) | FREE Enjoy Chicago's beloved sky spectacle show every Wednesday night at 9pm and Saturday night at 10pm,... Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy.
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Now in its 83rd season, Shoreline Sightseeing operates Chicago's largest and most diverse fleet of cruise boats and water taxis with 11 major tour vessels and 7 water taxis. Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with fabulous light show, at Navy Pier. Our Skyline Lake Tours only depart from our Navy Pier dock at 600 E. From Navy Pier, you’ll head out on a majestic boat tour of Lake Michigan where you’ll be able to see Chicago’s renowned skyscrapers and landmarks light up.
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. Starbucks Coffee, Twinings Tea, Coca-Cola soft drinks and lemonade are all complimentary.

Listen to seasonal music and celebrate the kick-off of the holiday season. Alcoholic and non-alcoholic beverages are available for purchase and Wendella will provide complimentary hot apple cider, hot cocoa, and sweets! Due to the timing of the cruise, you will not see the parade from the boat. History comes alive on this exciting Windy City boat tour.
• Wednesday departures are 2 hours.• Saturday departures are approximately 2.5 hours (depending on lock traffic). Our Skyline Lake Tour takes you on a loop around Lake Michigan, heading both north and south on the lake, you’ll see many of Chicago’s famous landmarks and the classic skyline vista. Take in the world-renowned architecture as our expert guides tell the story of 130 years of architectural innovation.
It was a gorgeous summer late afternoon and the city was just sparkling. I thought the price was great for the experience. The Tall Ship Windy is a must thing to do at Navy Pier.
There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy. No matter where your compass points, we’re here to create more unforgettable memories with you. For parties up to 170, we have fully-outfitted boats and onboard amenities to help you create a private event they’ll talk about for years to come.

We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024. Tall Ship Windy offers an unforgettable sailing experience. Explore Chicago’s Skyline and choose from Sunset Sails, Skyline Sails and Educational Sails. The journey begins at the Chicago Riverwalk, cruises up and down the main branch of the Chicago River, and ends with a spectacular view of the Chicago Fireworks as seen from the Chicago River. AMDI anticipates a public offering price between $3.50 to $4.50.
2024 Chicago New Years Eve Cruise – The Midnight Kiss 12/31/2023 - Choose Chicago
2024 Chicago New Years Eve Cruise – The Midnight Kiss 12/31/2023.
Posted: Sun, 31 Dec 2023 08:00:00 GMT [source]
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. I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time.
There is also a restroom available on board. There is no narration, but light music for you to enjoy as the vessel cruises up and down the Chicago River. Join Chicago Water Taxi on Wednesday and Saturday nights as we depart from the Riverwalk to view the City’s magnificent fireworks display. Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan. Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer.
Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy. 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.
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