Tall Ship Windy

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 Mondays left this season: 8/24 & 8/31, 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!