THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Enjoy live blues music aboard the Tall Ship Windy on a 2-hour Monday night concert sail. Discover stunning Chicago skyline views in a lively, relaxed setting.
Enjoy live blues music aboard the Tall Ship Windy on a 2-hour Monday night concert sail. Discover stunning Chicago skyline views in a lively, relaxed setting.
Book with Tall Ship Windy
Verified experiences and guided adventures in the surrounding area.
Operated by Tall Ship Windy · Chicago, Illinois
Set sail on an unforgettable 2-hour boat tour every Monday this summer aboard the Tall Ship Windy, right in the heart of Chicago, Illinois. The Monday Night Concert Series - 2025 offers a unique blend of live blues music and breathtaking views of Chicago’s iconic skyline. As the ship glides along Lake Michigan, you'll enjoy the soulful sounds of talented artists paired with a full bar and a relaxed atmosphere. Whether you're looking to unwind after a long day or enjoy a lively evening out, this private boat tour creates an exceptional experience that turns your Monday into a highlight of the week. The historic tall ship adds charm to the event, inviting both locals and visitors to celebrate Chicago’s vibrant music scene while soaking in the summer breeze. With limited spots available, this concert sail is perfect for friends, couples, and music lovers eager to experience the city from a refreshing new perspective. Don’t miss this chance to combine an outdoor adventure with a cultural outing on the water.
easy.
2 hours.
No special fitness level required; easy for most ages and abilities as the tour is seated and relaxed.
Tickets are refundable if cancelled at least 48 hours before the scheduled departure due to weather or personal plans.
Yes, the concert series is family-friendly, but alcohol is only served to guests 21 and older.
Outside food and beverages are not permitted; a full bar and snacks are available for purchase onboard.
Yes, seating is provided for all guests, with options both on deck and in sheltered areas.
In case of severe weather, the sail will be cancelled and you will receive a full refund or option to reschedule.
Boarding takes place at Navy Pier in Chicago; detailed directions and a map are provided upon ticket purchase.
Tall Ship Windy reflects Chicago’s maritime heritage, preserving traditional sailing vessels on Lake Michigan.
The company practices eco-friendly operations to minimize fuel use and protect lake water quality.
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