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This one departs from Seadog’s dock at Navy Pier throughout the summer months. 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.
Our Cruises & Tours
Being onboard is sure to be an experience you'll never forget. 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. 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. Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer.
Highlights of this tour
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. 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.
Choose Tall Ship Windy For Your Special Event
This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. Explore Chicago’s iconic architecture aboard TripAdvisor’s #1 rated boat tour of the city. The only Chicago River cruise partnered with the Chicago Architecture Center (CAC), Chicago’s First Lady Cruises offers visitors the city’s most engaging 90-minute architectural tour experience.
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Wind-down from the work-week by enjoying a cocktail with friends and family and experience Chicago's skyline on our luxury boats. Hosted on the bright red Fred A. Busse Fireboat – which served the Chicago Fire Department until 1981 – this architectural tour of the Chicago River lasts anywhere from 90 minutes to two hours. A docent will fill you in on the history of buildings lining the river as well as the story of the boat you've boarded, which formerly traveled the city's waterways to fight fires. If you're looking for dinner with a view, you could do worse than watching the sunset against the skyline aboard this 2.5 or 3-hour Lake Michigan brunch, lunch, or dinner cruise.
Seadog River and Lake Architectural Tour
If you’re looking to still have some kind of tour, you can hire a personal tour guide—and we haven’t even gotten to the best bit. These boats are all electric, so they’re a little bit more environmentally friendly, too. How do you end the perfect day of sightseeing? There are few more iconic Chicago sights than seeing the bright yellow Seadog speeding around town. And after this blustery 75-minute tour has finished traversing the Chicago River, it ends with a thrilling whizz across Lake Michigan, past Museum Campus, and Grant Park.
Guests who are able to transfer may use the company's manual wheelchair based on availability.Visit our accessibility page for more information. Our sister company, Mercury, offers the popular Canine Cruise on summer weekends. If you’d like to take a lake tour, please check out our sister cruise line Mercury, Chicago’s Skyline Cruiseline. We are happy to offer free foreign language audio guides in Spanish, French, Japanese and Korean. Advance reservations are recommended as many tours sell out during the busy summer season and on weekends.
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. Chicago's Leading Lady, Chicago’s Classic Lady, and Chicago's Emerald Lady are wheelchair-accessible. These vessels cruise at the 9am, 10am, 11am, 12pm, 1pm, 2pm, 3pm and 5pm departure times. When boarding, guests cross two ramps and enter through a 36-inch-wide opening (doorway). Crew members will assist in guiding the wheelchair across the gangway.
Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for two-hour trips along the Chicago River. The reservation comes with a premium drinks package and you can also opt to kick things up a notch with picnic baskets full of food or full-service catering. If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park, and more.
Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood. TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour. Learn about the architects who created our city's magnificent buildings—and the stories behind them. Experience why the CAC's boat cruise is rated the best year after year. Led by the Chicago Architecture Center's expertly trained docent volunteers, this 90-minute cruise reveals fascinating stories behind Chicago's majestic buildings in a way no other tour can. It was a very educational and relaxing seventy-five minutes.
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If you have limited mobility, see these directions for an alternative way to reach the dock. Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions. Sign up for our email to enjoy Chicago without spending a thing (as well as some options when you’re feeling flush). Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy. AMDI anticipates a public offering price between $3.50 to $4.50.
With its variety of tour options, cruise times and lengths, and a heated, enclosed cabin, Wendella is a great choice for families looking for flexibility. Choose from lake & river architecture, sunset cruises, and more. Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or... Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible... That’s what’s on offer with this Chicago River tour.
Please present yourself to our staff if you prefer to board before general boarding starts. Guests unable to climb stairs to the upper deck may choose to sit in the open-air bow or the enclosed, climate-controlled salon with large windows. For safety reasons, motorized scooters and electric wheelchairs cannot be accommodated.
Interested in a tour for a group of 20 or more? Please contact our group sales team at Private rentals are available. There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy. There is enough seating for all guests to sit on our open air upper decks safely and with proper distancing measures in place.
Everyone should be able to enjoy our tours. Mercury Cruises also offer Urban Adventure, Canine Cruises, and Chicago by Night tours. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides.
Take in the city’s magnificent architecture bathed in golden light as it begins its transition from day to night. The city's most popular tour is now offered in the evening. Serene and bathed in softer light, the city's architecture takes on a whole new life in the setting sun.
