Tall Ship Windy

Tall Ship Windy See Chicago from the water ⚓️
Skyline sails, fireworks cruises, live music & unforgettable summer nights from Navy Pier. Celebrating 30 years on Lake Michigan ✨

06/19/2026

Monday nights hit different on Tall Ship Windy.

Join us for live music from Michael Charles while sailing along Chicago's iconic skyline. Enjoy an unforgettable evening on the water with great music, lake breezes, and some of the best views in the city.

🎶 Live Music
⛵ Sailing Aboard Tall Ship Windy
🌆 Chicago Skyline Views

Every Monday from 7 PM - 9 PM.

Reserve your tickets: https://lakeshoresail.com/sailing-experiences/monday-night-concert-series-2026/

06/12/2026

Turns out I didn’t need to fix my life… I just needed sunshine, fresh air, and a sailboat. ☀️⛵️

Our crew was interviewed, it is was aired, but you can still heat it here. They have posted the recorded show, look for ...
05/29/2026

Our crew was interviewed, it is was aired, but you can still heat it here. They have posted the recorded show, look for this show from 5/29: "Say More with Mary Dixon and Patrick Smith"
It is spread out over the hour show.

Chicago looks different from the water.No crowds. No traffic. Just the skyline, the lake, and a little space to take it ...
05/28/2026

Chicago looks different from the water.

No crowds. No traffic. Just the skyline, the lake, and a little space to take it all in.

If you haven’t done it yet, sailing on Windy is one of those experiences that’s worth it.

Book your sail today: lakeshoresail.com

05/27/2026

Imagine this being your Wednesday night 🥹✨

Fireworks cruise tonight at 9PM 🎆

Memorial Day weekend is one of the best times to be on the water in Chicago.Longer days, great weather, and the city sta...
05/25/2026

Memorial Day weekend is one of the best times to be on the water in Chicago.

Longer days, great weather, and the city starting to come alive for summer.

If you’re looking for something different to do this weekend, a sail on Tall Ship Windy is hard to beat.

Bring friends, bring family, or just come out and enjoy the lake.

lakeshoresail.com

Address

700 E Grand Avenue/Navy Pier
Chicago, IL
60611

Opening Hours

Monday 10am - 7pm
Tuesday 10am - 7pm
Wednesday 10am - 7pm
Thursday 10am - 7pm
Friday 10am - 12am
Saturday 10am - 9pm
Sunday 10am - 7pm

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