THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Experience Chicago’s 2025 Air & Water Show from a luxurious yacht with uninterrupted views of aerial stunts and water performances. A perfect way to enjoy this summer event from the water.
Experience Chicago’s 2025 Air & Water Show from a luxurious yacht with uninterrupted views of aerial stunts and water performances. A perfect way to enjoy this summer event from the water.
Book with Tall Ship Windy
Verified experiences and guided adventures in the surrounding area.
Operated by Tall Ship Windy · Chicago, Illinois
Join Tall Ship Windy for an exclusive 3-hour boat tour aboard a luxurious 148-foot yacht during Chicago’s iconic 2025 Air & Water Show. Departing directly from Navy Pier, this special event offers unsurpassed waterfront views of thrilling aerial acrobatics and dynamic watercraft displays. Onboard, guests enjoy comfortable seating, fresh lake breezes, and an intimate setting perfect for families, friends, or private celebrations. As the jets roar overhead and boats perform daring stunts nearby, the vibrant energy of this summer spectacle comes alive surrounded by the city’s stunning skyline. This unique maritime vantage point provides a front-row seat to Chicago’s most anticipated summer event, combining excitement and relaxation on Lake Michigan. Whether you’re a local or visiting, this adventure offers an unforgettable way to experience the Air & Water Show beyond the crowded shores, making it an essential addition to your summer plans.
easy.
3 hours.
Suitable for most fitness levels since the experience involves relaxed seating onboard with minimal walking.
Tall Ship Windy does not permit outside food or drinks; however, beverages can be purchased onboard.
Yes, this is a family-friendly event suitable for all ages with safety measures in place.
Tours may be canceled or rescheduled due to severe weather; you will be notified in advance for refunds or alternatives.
The boat departs from Navy Pier in Chicago, a central and accessible location.
Yes, life jackets are available onboard and required to be accessible throughout the tour.
Yes, several parking garages are located near Navy Pier with both hourly and daily rates.
Navy Pier has been a central Chicago landmark since 1916, evolving from a shipping and recreational hub to a premier event destination.
Tall Ship Windy follows eco-friendly operational practices to minimize impact on Lake Michigan’s water quality and local wildlife.
Tall Ship Windy is a Chicago-based sailing experience operating on Lake Michigan. The vessel hosts a range of public sails, private charters, and special-event cruises that showcase Chicago’s skyline, fireworks displays, air and water shows, and competitive SailGP racing. Signature offerings include a 75-minute Chicago Skyline Sail available daily from May through October, a 90-minute Fireworks Cruise at sunset, themed concert sails such as Traditional Chicago Blues with Michael Charles, and seasonal Independence Day and Air and Water Show specials departing from Navy Pier. Tall Ship Windy partners with other providers for select activities, including stand up paddleboarding lessons promoted through Coastline Adventures, and offers add-on options such as boxed charcuterie and cheeseboards to elevate onboard hospitality. Certain special events use a 148-foot yacht for premium viewing and access to Race Village during Sail Grand Prix weekends. The operation emphasizes unique vantage points from the water, combining sightseeing, live entertainment, and curated food and beverage options. Guests can expect scheduled public departures for signature sails, plus options for private and semi-private bookings for lessons and charters. Event descriptions list duration and seasonal availability where applicable. Tall Ship Windy appears in The Adventure Collective directory as a provider of maritime experiences in Chicago, presenting a reliable way to experience major city events from the water. Bookings are recommended early for high-demand dates such as Air and Water Show, SailGP, and Fourth of July cruises. Tickets often sell quickly for signature dates, so checking availability and booking in advance is advised today.
Book with Tall Ship Windy