Tall Ship Windy

09/02/2026

🎸 This is your last chance to experience the Monday Night Concert Series in 2026!

Join us aboard the 148-foot Tall Ship Windy for one final evening featuring Michael Charles and His Band, breathtaking views of the Chicago skyline, and a full bar onboard.

⛵ Monday from 7–9 PM
🎶 Live blues and rock music
🌆 Incredible skyline views
👨‍👩‍👧‍👦 All ages welcome

Tall Ship Windy is about to dock for the year, so don’t miss your chance to sail with us before the 2026 season ends. Tickets are limited, so book yours today!

Book now: https://lakeshoresail.com/sailing-experiences/monday-night-concert-series-2026/

Celebrating 30 years on Lake Michigan, Tall Ship Windy invites guests to enjoy skyline sails, fireworks cruises, special event sails, group outings, and private charters from Navy Pier.

09/02/2026

There’s nothing quite like watching the Chicago skyline glow gold while a live band plays behind you! ⛵🎶

This Friday, September 4th, join us for a Live Music Sail featuring Michael Charles! We will be sailing from Navy Pier, 7:00–9:30 PM.

Grab your crew, grab a drink from the bar, and let the lake do the rest.

🎟️ Tickets link in bio

09/02/2026

Even the jet skis had to pull up for this one 😂🎶⛵️

Live music. Chicago skyline. Sunset over Lake Michigan. And apparently, a few unexpected guests stopping by for the show.

This Friday is our LAST Live Band Sail of the season! 🌅🎸

Come experience one final summer night on the lake with us.

🎟️ Tickets available on our homepage!
lakeshoresail.com

08/24/2026

If you love live music, you need to see this 🎶⛵
A live band, the Chicago skyline, and Lake Michigan at golden hour, every Monday night! One of the most relaxing ways to spend an evening in this city.

Only 2 Mondays left this season: 8/24 & 8/31, 7pm.

Link in bio to book

🎸 Michael Charles

08/24/2026

There’s a sailboat in Chicago with a live blues band every Monday night 🎶⛵
JBTV’s Blue Channel came out and filmed it. This is the 35-second version, the real thing is a 75-minute sail on Lake Michigan with the band playing live the whole way.

Only 2 left this season: 8/24 & 9/4, boarding at 7pm.
Tag the friend you’re bringing. Link in bio to book.

🎥 JBTV Music Television
🎸 Michael Charles

08/11/2026

See the Chicago Air & Water Show from Lake Michigan aboard Tall Ship Windy!

Join us August 15–16 for a special 2.5-hour sail departing from Navy Pier. Choose from morning or afternoon departures and enjoy incredible views of the show and Chicago skyline.

Tickets are limited and these sailings typically sell out. Reserve your spot today!

🎟️ Book now: https://lakeshoresail.com/sailing-experiences/chicago-air-water-show-2025/

Experience the Chicago Air and Water Show 2026 from the water! Book your boat with Tall Ship Windy Chicago for a front-row seat to the thrilling action!