Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Recommended by 90% of travelers

Chicago, USA

1 hour 15 minutes (approx.)
Offered in: English

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Overview

There are many spots around Chicago where you can take in views of the city, but setting sail on Lake Michigan lets you take in the full scenic skyline. On this boat tour, hop aboard a traditional vessel and learn how to hoist a sail, or just relax on board at the fully stocked bar.

Pick up some souvenirs to remember your trip at the on-board gift shop
A great way to socialize with fellow travelers
The perfect vantage point to snap photos of the Chicago skyline
The crew will happily answer any questions throughout your trip

What's Included

Restroom on board

Alcoholic Beverages
Snacks
Gratuities

Meeting and Pickup

Meeting point

600 E Grand Ave, Chicago, IL 60611, USA
Tall Ship Windy, is located near the Billy Goat Bar and Grill

End point

This activity ends back at the meeting point.

Itinerary

Chicago Skyline (Pass By)

Navy Pier (Pass By)

Lake (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Service animals allowed

Near public transportation
Travelers should have a moderate physical fitness level
This tour/activity will have a maximum of 150 travelers

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Cancellation Policy

This experience is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

4.8

based on 20 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

wonderful Windy

Allison_M, Sep 2025

This was a lot of fun. The crew was all very engaging but was all business when it was time to raise or lower the sails. Granted we had a perfectly clear and windy day, but the sailing conditions were perfect. As someone from the east coast, it's hard to fathom that we were on a lake, not the ocean. The only complaint was it could have been longer.

Book it!

Amanda_D, Aug 2025

What a great sail. Nice ship. Nice crew. Great experience. It’s a little pricey, but views of skyline are priceless!

There was no narration...

Barbara_L, Aug 2025

There was no narration and they did not sail. It was motorized not sail powered. This was poorly advertised.

Response from Host, Aug 2025

Where did you learn that these were all narrated? We attempt to sail EVERY sail, and while the ship may be running, we do try to keep some speed on the vessel, lest we just rock on the waves in place. as for the other issue, we offer non-narrated, quiet sailing sails, for those seeking just that.

Very cool experience. If...

Megan_S, Aug 2025

Very cool experience. If you get sea sick, be sure to take Dramamine. You can help raise the sails and even drive the boat. It was a beautiful view of Chicago.

Quirky but worth it

Marylou_D, Jul 2025

Nice ride that felt about the perfect length to head out on the water and back. Good for sunset skyline shots. No serious waves as it's inside the break wall ~1/2 the time, and can see land/buildings & other boats the whole time, so should not have to worry about nausea. Volunteering is encouraged for hoisting the sails with preference given to kids. There's a clean restroom on board if needed. The crew take their job very very very seriously (literally make you take the stairs backward and pretend they are a "ladder"), but otherwise seemed like a flamboyant improv troop. There's a bar, but drinks are pre-made watered-down pours for ~$12; ok if you're thirsty in the summer but otherwise would probably wait till later. Overall, worth the money and would recommend if you can go with the flow and climb stairs backwards.

Likely to Sell Out