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 ✨

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

05/24/2026

Nothing like Memorial Day weekend on the water ⚓️✨

05/23/2026

Michael Charles LIVE on Windy

Join us tonight at 7 PM for an unforgettable evening of blues music on Lake Michigan with Chicago’s skyline as your back...
05/22/2026

Join us tonight at 7 PM for an unforgettable evening of blues music on Lake Michigan with Chicago’s skyline as your backdrop ⚓🎶

Then come back tomorrow night at 9 PM for fireworks over the water.

There is nothing quite like summer aboard Tall Ship Windy.
lakeshoresail.com

Opening weekend is here, and it’s already happening.People are back on the water, drinks in hand, skyline behind them, a...
05/21/2026

Opening weekend is here, and it’s already happening.

People are back on the water, drinks in hand, skyline behind them, and that first real taste of summer kicking in.

If you’re not out here yet, you’re going to start seeing it everywhere.

Don’t be the one watching from shore: lakeshoresail.com

Opening Day is officially in the books ⚓A huge thank you to our incredible crew for helping kick off another season on L...
05/19/2026

Opening Day is officially in the books ⚓

A huge thank you to our incredible crew for helping kick off another season on Lake Michigan. We are excited to welcome guests back aboard Tall Ship Windy for our 30th season of sailing in Chicago.

Here’s to skyline views, lake breezes, unforgettable sails, and an amazing season ahead.

📸photogenic

Our 30th season celebration is officially underway.That means special offers on select sails, including skyline and fire...
05/18/2026

Our 30th season celebration is officially underway.

That means special offers on select sails, including skyline and fireworks experiences.

If you’ve been thinking about booking, now is a great time to take advantage.

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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