Tall Ship Windy
Tall Ship Windy
4.5
10:00 AM - 9:00 PM
Monday
10:00 AM - 7:00 PM
Tuesday
10:00 AM - 7:00 PM
Wednesday
10:00 AM - 9:00 PM
Thursday
10:00 AM - 9:00 PM
Friday
10:00 AM - 9:00 PM
Saturday
10:00 AM - 9:00 PM
Sunday
10:00 AM - 9:00 PM
About
Tall Ship Windy is Chicago's Official Tall Ship! Many sailing trips daily, May - Sept 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
Chicago, Illinois

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Tours and Tickets by Tall Ship Windy
1–2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 90% of travelers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
$49.00
per adult
2 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 92% of travelers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
$79.00
per adult
Travelers talk about
(107 reviews)
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions

4.5
1,457 reviews
Excellent
1,089
Very good
218
Average
71
Poor
38
Terrible
41

jnedrud
Minneapolis, MN1 contribution
May 2022 • Family
Our family had a great time sailing with Tall Ship Windy. The day was beautiful and the wind was strong. The crew made the experience interactive for our kids, letting them help hoist the sails and steer the rudder at various points. The crew was knowledgeable and told tales of sailors gone by. It was a wonderful time.
Written June 7, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Capt_Bruce_R
We love our Sailor/Pirate excursions the most; so much fun and history to share! Please join us again.
Written June 13, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Chantal M
Chicago, IL74 contributions
Sep 2020
We sailed Tall Ship Windy for their educational sail. It was wonderful. What a great field trip idea. We had kids from PreK to highschool. All of them were engaged and learned something new about the pirates that used to sail lake Michigan. I would highly recommend this.
Written September 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Kari S
Milwaukee, WI189 contributions
Aug 2022
This felt like the best choice of all boat tours in Chicago and wow, that's the truth! We did the sunset sail and it was beautiful...surreal. The Chicago skyline is amazing at sunset and the ship with the sails up was breathtaking. There is a bar on board, which was nice to have a drink while sailing.
Written August 29, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
tickets t
YEAH! We are thrilled to hear how much you enjoyed your sailing charter with Tall Ship Windy! Join us another time soon!
Written August 29, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Barbara K
Chicago, IL57 contributions
Sep 2021 • Couples
Fireworks cruise - amazing BEST place ever to watch fireworks ever for me. Loved the view, be sure to ask where to sit for the best view of the fireworks, ours was superb. Close by fireworks (and not skimpy I will add!) with the city of Chicago as a backdrop, worth every penny. We had VIP tickets which I think just meant we got to get on the boat first!? First choice of seats. Fireworks show was superb and then just a short sail.
Written September 12, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Melissa R
Yes! We are so thrilled you had the BEST place to view the fireworks and got to get out on the lake! We always want for everyone onboard to have a superb tie and we are happy to know we did not disapoint!
Written March 12, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Allan R
15 contributions
Jun 2021 • Couples
Went on a Saturday evening tour. Get views of downtown Chicago not available anywhere else. Lovely large ship with very friendly crew. Good mix of folks onboard, we had a great time. Well worth the recommendation!
Written June 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Coloradoroadtripper
Gunnison, CO14 contributions
Despite tornado warnings for the city and counties in a 50 mile radius, despite a power outage in Chicago, despite traffic at a stand-still and warnings not to travel, Captain Bruce refused to give a refund for the trip. Shocking, irresponsible, and very disappointing,
Written June 29, 2010
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

BVnLJ
Cheswick,Pa.156 contributions
My wife and I wanted to see the Navy Pier and we discovered this very cool attraction. Once my wife seen the ship we just had to go and it did not disappoint. We took the fireworks cruise. The view of Chicago from the lake at night was awesome. We headed out at dark under diesel power then once we cleared the docks the sails went up. We did not get an opportunity to raise the sails to many volunteers. After a harbor cruse the fireworks started. It was great to see the city as a backdrop to the fireworks. The crew was excellent. I don’t know how the captain navigated the harbor with all the other boats around the man deserves a raise. We would recommend this attraction for the fireworks cruise or the pirates cruise. September 18/2009
Written October 4, 2009
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

JGM79
Chicago, IL2 contributions
I bought Groupons for a non-primetime sail which was stated on Groupon as sail before the 5 pm evening sail. When I went to use the groupons yesterday for a noon sail, I was charged additional money and told that the noon sail is a primetime sail. This was not stated on Groupon and I informed the attendant that charging additional funds is false advertising which is illegal. It is a shame I had this experience because I really enjoyed the sail but will warn others against their false advertising practices.
Written July 20, 2010
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
This review should have been about Groupon, Not Windy, we offered and provided a great time.
Written September 1, 2010
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

JeffCinDC
Washington DC, DC44 contributions
Jun 2017 • Couples
Wow, never seen anything like it. We were ready to go, light breeze, sun, but storms in the area. They advertised they sail rain or shine, and thus if we cancel, there are no refunds.

But we didn't cancel, they cancelled. For our safety. Fair enough, but also for the safety of their vessel, and for the liability they'd face if they sailed and people were injured. They offered to take us the next day, but we'll be in DC.

No refund? You've got to be kidding. I called VISA and they said they'd reverse the charges. Tall Ship Windy needs to adjust their policy.
Written June 19, 2017
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Tall Ship Windy strives to provide a safe and enjoyable experience. Tall Ship Windy offers trip insurance to all, who sail with us, for all who can't reschedule, and for the reasons stated like above. If they had purchased it, they would have been given a full refund. It is unfortunate situation, where in hindsight, they should have purchased insurance, and they're blaming us for our clearly stated "no refund" policy. AND to be clear, by the time management heard about this, he had already called his credit card company, leaving us no options.
Written June 21, 2017
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Shioban L
2 contributions
Jul 2020 • Friends
Don't support this business. We pre-booked a large party weeks in advance for my friend's husband's 35 birthday. The time came for our group to board and they only had reservations for half our party. They had an issue in their system and instead of them taking care of our group who pre-purchased and showed proof of said purchase they continued to let people board. My girlfriend was literally in tears. Totally unprofessional I would not ever book services with them.
Written July 18, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Capt_Bruce_R
We regret your tickets did not include your entire party and that we had to make adjustments to your boarding. As you booked with a third party agency, we were just as surprised by the overbooking you experienced.
Written June 17, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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Tall Ship Windy (Chicago) - All You Need to Know BEFORE You Go