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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most fitness levels since the experience involves relaxed seating onboard with minimal walking.
Wildlife
History
Navy Pier has been a central Chicago landmark since 1916, evolving from a shipping and recreational hub to a premier event destination.
Conservation
Tall Ship Windy follows eco-friendly operational practices to minimize impact on Lake Michigan’s water quality and local wildlife.
Tall Ship Windy
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.
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.
Location
Chicago, IL
Departures from Navy Pier for several events
Schedule
Daily (May–Oct)
Skyline Sail operates daily May–October
Vessel Size
148 ft (special events)
Used for premium event viewing
Featured Events
Air and Water Show, SailGP, 4th of July
Seasonal, high-demand event sails
Book skyline sails, fireworks cruises, and special-event voyages now — limited capacity on popular dates.
Arrive Early to Dock at Navy Pier
Plan to arrive at least 30 minutes before departure to ensure a smooth boarding process at this popular location.
Wear Comfortable Footwear
Non-slip shoes will keep you steady on the yacht’s deck while moving around during the show.
Bring Sunglasses and Sunscreen
Protect your eyes and skin from the summer sun while enjoying the open water views.
Keep Binoculars Handy
Binoculars can enhance your viewing experience, allowing you to catch details of the aerial maneuvers far above.
Lightweight Jacket
Lake Michigan breezes can be cool even on warm days, so a jacket helps stay comfortable.
summer
Sunscreen
Protect your skin from prolonged sun exposure during the trip.
summer
Binoculars
Improve your view of distant aerial stunts and watercraft.
Camera
Capture stunning photos of the show and Chicago’s skyline.