Great staff, very much offering the guests the ability to participate in the raising of the sails. It was very much like what the description offered. Our experience was at 7pm on Labor Day Sunday. Watching the sun set behind Chicago’s skyline and then the twinkling lights was magical. Wear rubber souled flat shoes for best stability on the ladders to the fore and aft decks. Best way to get there is via Rideshare mid-Navy Pier drop off.
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"





Description
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ages! You can join our friendly crew, to help raise one of the many sails on Windy, or just relax, and let others do the work! Windy has a full bar, and a gift shop, to help you enjoy the sail.
Tour Options
Itinerary
You'll enjoy a quiet sail, on Tall Ship Windy, while taking in the great views of Chicago famous skyline from the lake!
Great view from the lake, and you will also board and return here.
We will be sailing on Lake Michigan!
Highlights
What's included
Traveller Ratings
Important Information
- Service animals allowed
- Public transportation options are available nearby
- Travelers should have at least a moderate level of physical fitness
Reviews(29)
Had a great time! Crew was very friendly and as a first time visitor to Chicago, it was awesome to see the city skyline from the sea.
Did the pirate story tour but I was just there for a ride on a beautiful tall ship, great view of the Chicago skyline, friendly crew.
A wonderful way to see the Windy City on a beautiful day! The tall ship was so wonderful, as was the friendly crew! Super fun activity!
Great way to spend a morning or afternoon! Super relaxing and fun. The crew was very friendly and let us raise the sails.
It was a heat wave in Chicago but the Windy was an awesome time! Very windy on the lake but the crew were amazing! Everyone did a great job and let people help raise the sails and explained everything. Highly recommend!
Friendly and knowledgeable Captain and crew. I had the opportunity to host the sails and take the helm and they even helped with pictures.
Awesome fun relaxing the crew was hilarious. Kid friendly big sailboat lots of room. Really good experience! We will be back
Great day on the water! The crew was friendly and helpful. The views of the Chicago skyline were spectacular. Sailing on a tall ship made it even more special, aye matey!
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.



