What to expect
- Learn what it was like to be a Tall Ship sailor on this fun and informative lake tour
- See and touch the tools of a sailor's trade and learn how they lived
- Follow the course of the wind on the Official Flagship of the City of Chicago
- Relax on the deck or join in the fun for an unforgettable experience
About this Activity
You'll get to see and touch the tools of a Tall Ship sailor's trade and learn all about their everyday lives from Windy's experienced crew-educators. Take in the beautiful Chicago skyline on the Official Flagship of the City of Chicago.
But if you'd rather just take a nap on the deck, thats ok too!
Note: Passengers must be able to navigate six steps up and one large step down.
|Price||$30.00 per guest|
|Duration / Session||75 min|
|Rating||18 positive reviews|
Janet M.Chicago Skyline Cruise May 23, 2021
Beautiful views! Fun trip!
Lev N.Chicago Skyline Cruise August 12, 2019
Excellent in any sense.
Charles C.Chicago Skyline Cruise September 19, 2017
Great staff and perfect amount of time. No scams anything additional was totally up to you
Abigail J.Chicago Skyline Cruise September 2, 2017
Really relaxing to be on the water, and some fun pirate storytime with Zach. Thanks for a great time!
Tony S.Chicago Skyline Cruise August 21, 2017
Great staff! Very nice short cruise for a scenic view of our City!!
Marion B.Chicago Skyline Cruise August 12, 2017
the sunset cruise was stunning, talented friendly staff, a very capable captain. we left the pier, raised the sails and had a delightful sail looking at the Chicago skyline, bartender was great he made mermaid drinks, that were a rum coconut pineapple concoction, extremely tasty. Just a wonderful adventure and very reasonably priced.
Marina G.Chicago Skyline Cruise August 10, 2017
Pirate Horns did an amazing job telling pirate stories with jokes for adults as well as the kids. He really made this experience memorable! Kids loved the ship, pulling the sails, and the beautiful Chicago scenery.
BiggJoeb .Chicago Skyline Cruise August 10, 2017
Great experience on the boat..cant believe iv never gotten on this before...30 bucks a person for 75 min on the lake I suggest going on the 9 o'clock trip better pics guaranteed . It's a hands on experience all the way...bar downstairs. Will definitely be back
Lori K.Chicago Skyline Cruise August 4, 2017
A nice relaxing trip. This is a fun activity for any age. We did the pirate cruise but they offer other themed trips. You set sail from the docks at Navy Pier. You can get some beautiful pictures of the coastline while enjoying a tasty beverage on the water. Buy a drink/snack card at the ticket booth. You'll save a few dollars. You can help hoist the sails, listen to true pirate tales and if you ask nicely the captain will let you take the ships wheel for a quick pic. I suggest getting a seat on the foredeck (front) if possible and if you want a drink get it as soon as you get on otherwise you'll wait in line for a bit. It would have been nice if the pirate stories were told over the speakers instead of just on the main deck. Overall a great way to spend some time on the water away from the busy city.
Grace C.Chicago Skyline Cruise July 8, 2017
This is was a BLASTTTTT!!! Other story about the pirates in Chicago were much more interesting than expected. I learned a lot about the history. I would honestly do it again just because it was funny and informative. Great for kids and adults. They have a bar!!! Win!!
Tracy M.Chicago Skyline Cruise July 7, 2017
Wonderful serene trip on the lake, we enjoyed every moment as well the beautiful skyline and the ability to see three states...
Great way to see the sunset over the Chicago Skyline
Carol M.Chicago Skyline Cruise June 19, 2017
This was a great tour. We took my grandfather for fathers day and he was just having a blast. I would suggest you buy a drink ticket in advance since you can save $2 that way and also the drinks are pretty fairly priced, usually I am used to paying $4 when I go to the zoo and want a gatorade, here on the boat it was only $2, which was great since it was a warm day. It was pretty cool to be on a sailboat and the tour provided some great information that I didn't even know about my own city! Kids would also love it!
Jessica D.Chicago Skyline Cruise September 2, 2016
Was able to order 10 tickets without any issues. Aug 31st, was the last firework show of Navy Piers season. Was very excited they still had availability. Being a full working wooden ship we could feel the "chopy waters". We where invited to help raise the sails! Since they are interactive and a teaching vessel.
Beautiful views, fun & funny crew. Very willing to work with us for pictures and making our experience fantastic!
They are very reasonable priced tickets! Worth every penny!
Ian S.A Sailor's Life for Me! Tall Ship Experience September 13, 2015
LaurLaw .Chicago Skyline Cruise August 12, 2013
What a great program to be able to sail on a tall ship and experience the views of the Chicago skyline. I was fortunate enough to be onboard for the fireworks and I feel like we had the best seats in the house. There is a bar available with drink purchases and the entire crew is enthusiastic. The Captain is friendly and available for questions. Highly recommend.
Ashley C.Chicago Skyline Cruise June 27, 2013
We sailed on the Windy today and had a fabulous time! The entire crew were amazing and really catered to the kids on the ship showing them sailing skills and allowing them to participate.
The views of the city skyline were beautiful and the ship was clean and safe. I highly recommend this trip if you are visiting or a local!
Ashley B.Chicago Skyline Cruise August 26, 2020
Did not leave comment
Teri B.Chicago Skyline Cruise September 4, 2017
Did not leave comment