Experience Chicago like never before on the Wednesday Fireworks Cruise. Sip drinks, enjoy sunset views, and watch Navy Pier’s famous fireworks from the water.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1.5 hours
Fitness Level
Suitable for all fitness levels as the cruise involves minimal physical activity and mostly standing or sitting.
Wildlife
History
Navy Pier, the backdrop for the cruise fireworks, was originally built in 1916 and has evolved into one of Chicago’s most beloved landmarks.
Conservation
Tall Ship Windy prioritizes sustainable boating practices to minimize environmental impact on Lake Michigan’s aquatic ecosystem.
Tall Ship Windy
Experience Chicago like never before on the Wednesday Fireworks Cruise. Sip drinks, enjoy sunset views, and watch Navy Pier’s famous fireworks 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 for Best Seating
Get to the dock at least 15 minutes before departure to secure the best viewing spot on deck.
Dress in Layers
Even summer evenings on Lake Michigan can get chilly, so bring a light jacket or sweater.
Bring a Camera with Image Stabilization
The boat’s movement can make photos tricky; stabilized gear helps capture sharp fireworks shots.
Avoid Large Bags
Space on deck can be limited, so bring minimal gear for comfort and mobility.
Light Jacket or Sweater
Keeps you warm during cool lakeside breezes, especially at sunset.
spring
Sunscreen
Protects your skin during daylight hours on the open water.
summer
Camera or Smartphone with Stabilization
Helps capture sharp photos of the fireworks and skyline despite boat movement.
Reusable Water Bottle
Stay hydrated while enjoying the cruise; water refill stations may not be available on deck.