We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
About Tall Ship Windy
Tall Ship Windy is Chicago's Official Tall Ship! Many sailing trips daily, May - Sep rain or shine! To see current schedule online, visit our website and click "buy tickets" We have a full service bar aboard This is a fun adventure, for all ages! Open May through September
Open Now
Hours Today: 10:00 AM - 9:00 PM
Certificate of Excellence
Travelers talk about
Improve This Listing
Tours and Tickets by Tall Ship Windy
Go Chicago Explorer Pass with SkyDeck and 360 Chicago
Discover the Windy City your way with a Go Chicago Explorer Pass. Valid for 30 days, the pass is ideal for travelers who want to take their time exploring the city. You can visit top attractions such as the SkyDeck, Field Museum, and Lincoln Park Zoo. You also have the option to choose activities, including a sightseeing cruise or hop-on hop-off bus tour.
Read more
30 days
from $66.00
Chicago Skyline Sightseeing Cruise
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
Read more
1 hour 15 minutes
from $33.60
Reviews (1,315)
Filter reviews
1,302 results
Traveler rating
Traveler type
Time of year
More languages
Traveler rating
Show reviews that mention
All reviews pirate stories lake michigan chicago skyline navy pier fireworks cruise great lakes sailing experience main deck friendly crew story telling architecture tour great adventure boat ride a lot of fun unique experience sails skiing
Selected filters
Updating list...
1 - 10 of 1,302 reviews
Reviewed November 20, 2019

We took friends who were visiting from out of state. This was our first time but we wanted to show them the Chicago skyline from the water. We were extremely pleased with the cruise. It was short enough but enough to see the skyline in...More

Date of experience: September 2019
Thank paojw
Reviewed November 13, 2019

What a unique, fun and beautiful way to explore Chicago!! The crew was excellent, the information was very interesting, and we even got to help hoist the sails and steer!

Date of experience: September 2019
Thank Candi F
Reviewed November 5, 2019

I purchased these tickets on Groupon and I couldn't be happier. I surprised my BFF girlfriend with this tour and plan to do it again next fall. The day was perfect with a blue sky, low humidity, a dash of clouds and perfect touch of...More

Date of experience: September 2019
Thank Alisa P
Reviewed October 28, 2019

We took the twilight tour on Tall SHip Windy in September 2019 whilst staying in Chicago, prior to starting Route 66. We are a couple in our 60's from England. You get the ship on the Navy Pier. The trip was about an hour long....More

Date of experience: September 2019
Thank Vonny1952
Reviewed September 26, 2019 via mobile

Touristy, but very fun! Our pirate-guide was personable and knowledgeable. In high season, buy your ticket early!

Date of experience: September 2019
Thank okie56
Reviewed September 25, 2019

The waiting wasn’t well organised: we had to ask where VIP priority boarding was as we couldn't see a sign, we had to go and get our tickets reprinted, as their scanner wasn't working and it takes ages to board because they photograph everyone getting...More

Date of experience: August 2019
Thank PotterMoose
Reviewed September 23, 2019

This was a fun short trip through Lake Michigan. "Ms. Kidd" told a fun story of pirates on the Great Lakes.

Date of experience: September 2019
Thank Jeremy B
Reviewed September 23, 2019

We had the pleasure to go out on the AJ Meerwald. It was docked in Cape May N J. It was a wonderful exciting experience. The staff were friendly, knowledgeable as well as experienced seamen!! We would highly recommend to all!

Date of experience: September 2019
Thank lovesfinedining14
Reviewed September 20, 2019

What a fun, unique way to enjoy Chicago's lakefront on a real topsail schooner! After boarding, we were invited to sit back and enjoy the narrated tour or assist the crew in raising the sails. There were so many great photo ops of the Chicago...More

Date of experience: September 2019
Thank mtnvu
Reviewed September 15, 2019

Spur of the moment trip downtown. It was going to be a beautiful day and we wanted to do something different. What a great choice we made picking a sail on the Tall Ship Windy. From the ticket window to exiting the boat all employees...More

Date of experience: September 2019
2  Thank Gina R
View more reviews
Questions & Answers
Ask a question
July 3, 2019|
AnswerShow all 2 answers
Response from 722jeremya | Reviewed this property |
I would message the company directly to ask. The website seems to say it is included. They are a small family owned business so it may be the web design that has a default button to purchase insurance not taking into account... More
May 24, 2017|
Response from Capt_Bruce_R | Property representative |
you can make reservation online. You do not have to reserve in advance, but we do recommend it. We have 3-5 people answering phones, if we don't answer, please leave a message.