Join the exclusive 4th of July Independence Sail on Chicago’s Tall Ship Windy for a VIP view of the city’s fireworks and skyline. Experience patriotic music, cool drinks, and stunning lake views in a unique boat tour.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels, minimal physical exertion required; mostly seated or standing on deck.
Wildlife
History
Chicago’s tall ship tradition dates back to its maritime roots as a Great Lakes shipping and trading hub in the 19th century.
Conservation
The Tall Ship Windy operates with eco-friendly practices, including waste reduction and the use of environmentally safe products to protect Lake Michigan.
Tall Ship Windy
Join the exclusive 4th of July Independence Sail on Chicago’s Tall Ship Windy for a VIP view of the city’s fireworks and skyline. Experience patriotic music, cool drinks, and stunning lake views in a unique boat tour.
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 Boarding
Plan to arrive at least 30 minutes before departure to allow smooth boarding and settle in comfortably.
Dress for Variable Weather
Even summer evenings on Lake Michigan can get chilly; bring a light jacket or layers.
Bring a Camera with Zoom
Capture stunning fireworks and skyline views without sacrificing image quality.
Avoid High Heels
Wear comfortable, flat-soled shoes for stability while moving on deck.
Light Jacket or Windbreaker
Keeps you comfortable against cool breezes on the water during early season sails.
spring
Sunscreen
Protects your skin from direct sun exposure during daytime and early evening hours.
summer
Comfortable, Flat Shoes
Provides stable footing on the ship’s deck and prevents slipping.
Camera or Smartphone with Zoom
Allows you to capture fireworks, skyline shots, and memorable moments.