Step aboard Chicago’s official tall ship for a variety of unique sails that combine hands-on sailing with panoramic city and lake views. Tall Ship Windy invites adventurers to experience Lake Michigan like never before.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; mostly standing or seating on deck with some light climbing on and off the ship.
Wildlife
History
Tall Ship Windy honors Chicago’s rich maritime heritage, sailing a classic vessel reminiscent of the city’s shipbuilding days in the early 20th century.
Conservation
The company promotes Leave No Trace principles on board and supports local lake clean-up initiatives to maintain Lake Michigan’s natural health.
Tall Ship Windy
Step aboard Chicago’s official tall ship for a variety of unique sails that combine hands-on sailing with panoramic city and lake views. Tall Ship Windy invites adventurers to experience Lake Michigan like never before.
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
Give yourself extra time before departure to check in and get familiar with the ship’s layout.
Dress in Layers
Lake Michigan’s weather can shift quickly; bring windbreakers and comfortable shoes with good grip.
Participation Optional but Recommended
Feel free to help raise sails for a hands-on experience, but you can also relax and enjoy the views from deck.
Bring a Camera
There are plentiful photo opportunities of Chicago’s skyline and lake vistas during daylight and special events.
Windbreaker Jacket
Protects against lake breezes and changing weather conditions on the water.
spring|summer|fall
Comfortable Non-Slip Shoes
Ensures safety and stability while moving around the ship’s decks.
Sunscreen
Helps protect skin from sun exposure during daytime sails.
summer
Camera or Smartphone
Captures stunning cityscape and lake views throughout the trip.