We purchased tickets for two and were thunderstormed out. A refund was refused but a new reservation was made and we were promised that our tickets would be honored anytime in the future. We arrived with our new reservation, which has a valid date and reservation #. We were told too bad! New Management, NO CAN DO! Well so much for our close to $ 100 spent on tickets. #bbb yup next stop better business bureau. So disappointed I guess it's true what they say about doing business in Chicago! Sincerely, a Canadian living in California. read more

I had found a voucher on the website, Social Living, so I thought what the heck, I'll try it. I'm glad I had bought it. The departure for this ship is half way down the pier, however, the pirate will alert you that this is the ship you want to ride. It's cheesy but..... Since it's still early in the summer season, I had plenty of time options so I decided on the 2:15pm. Prior to boarding the ship, the pirate will give the rules and regulations in "pirate talk". The ship was only half full. So there were plenty of seating areas. The ship has three large decks and full bar. Perfect sunny Wednesday afternoon. I forgot how long the cruise was. You will sail about half a mile south of the pier and then dock. You will have incredible views of the city - maybe I was expecting more sailing about the pier. But it was a great way to spend an afternoon. Check out their website to make sure this is the right cruise for you. They do have various cruises available. read more

See all

Gord and I did the 7:30pm sailing on the Tall Ship Windy. It was about $30 each and was about 75 minutes. The theme was "Real Pirates of the Inland Seas" We sat in the front (the bow). You could help raise the sails. Ben the Pirate told stories. The views were great and the sunset was fabulous. Gord and I love going on boat cruises and this one had the added bonus of the sunset. read more

See all

Fantastic time! Captain Bruce and the staff are very accommodating it is such a relaxing ride. Will return soon! So nice being out on the water with no motor noise. Just the wind and sounds of the city. read more

See all

Took some friends out for a swashbuckling good time aboard the Tall Ship Windy. We scored some Groupons which were easy to transfer to tickets on their intuitive online site. The only downside of ticketing was that their website states clearly you can screenshot your tickets for entry. When we arrived and got in line to board, we were told paper tickets only, so we had to get out of line and go back to the box office. So, bear this in mind! Non alcoholic drinks can be brought on board and there's a full bar beneath deck. They also have reasonably priced souvenirs, glasses, and cute hats. The cannon was a nice touch! We had a fun time! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

I went on the first sailing of the season, and had a fantastic time. You could see the experienced crew helping the new crew with various tasks but that just added to the experience. I love that they asked for volunteers to help raise the sails. They gave great training and explained why certain things were being done. The host on the mic was funny, friendly and helpful. I loved the pirate stories. The bar was well stocked and I liked the decor. I will definitely return read more

See all

We sailed on the 7 pm cruise on a Saturday evening, so it was not a "tour". I don't know if they offer any tours, but I enjoyed the peace and quiet of no motor and just the wind in the sails. If anyone is interested in assisting to hoist the sails, they are invited It is sort of a pirate theme with pirate flags flying, but only one person spoke like a pirate and was dressed the part. There is seating at the front and rear of the boat, and little people are required to stay in the middle section with an adult. Views are wonderful, but then, Chicago has a great skyline. Be aware, it can get breezy and cool, especially when the sun sets, so dress appropriately or carry a jacket. The staff at the ticket booth were very helpful. I had an issue with my phone so they just pulled up our confirmation and issued us our tickets. Painless. read more

Came aboard the Tall Ship Windy with a bachelorette party and had a blast! The crew was super fun and enthusiastic and we got some great views of the city along with some fun facts. Best part however, there's a BAR on the BOAT! Highly recommend this fun/educational event read more

It was a great experience for our family. The crew were so nice and knowledgeable. My kids loved being on a pirate like ship. The viewing was amazing. I would definitely return back and board on this ship again. read more

The tour was really great. They took our picture before we boarded, taught us sailing terminology, gave plenty of time for photo ops, and the crew were so kind. Only thing I didn't care for was trying to charge us 25 dollars for 3 pictures of us before we boarded. We only needed one and they said it's all 3 for 25 or nothing. They were nothing really special but for the price of the ticket I feel they should include the pictures as they already had them printed out and everything before you get back. Seems like you'd save more money printing them by request, then wouldn't have to charge patrons so much. read more

The crew enthusiastically set sail on time. We enjoyed incredible views of the Windy City before and after sunset. The music and Caribbean drinks added to a spectacular and memorable time!! read more

Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later. read more

we had a very enjoyable cruise with trustworthy and energetic crew. learned a lot about tying knots and pirate history. Only complaint would be that we thought we'd learn a little more about lake history and ecology based o. the promotional material: "This unique, hands-on learning experience is a great way to enjoy physics, ecology, history, and storytelling while taking an active part in sailing the vessel. " overall, a good-enough value and experience read more

I had a great experience riding onboard Windy. The crew provided a fun and interactive experience. I was given the opportunity to join in on hoisting the sails and there were many great photo opportunities. The crew is friendly and more than willing to help take photos. Definitely worth a better experience than a regular city cruise which has you just sitting down and listening. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

See all

The sunset time and the ship in general were fabulous and we had an amazing time. However, one note - I stood on line one hour before departure so my family and I could get a good spot to sit. We were the 3rd people to board and we got the seats with the view we wanted.. But then a group of 15 people boarded at the very end and came and stood right in front of us. They were drinking alcohol and being loud the whole time. I felt this was very unfair as it ruined the experience for me and my family. I wish the crew would be a little mindful of this and ask people to SIT somewhere instead of standing and blocking everyone else. read more

I took the Architectural Tour with friends on a trip to Chicago in July. Wonderful experience if you love being on the Great Lakes (I do), tall ships, and architecture. They ask for volunteers to help raise the sails and I did. Quite the workout! Thankfully you have help from others. The weather was perfect and I would definitely recommend it to anyone as a fun and educational city experience. (We took the water taxi to Navy Pier from near Union Station so water travel was kind of the theme of the day. That was fun too.) read more

Gone for a mini family vacation and needed something to do at night that would allow us to see the city lights. Tall Ship Windy was perfect! It's an actual sail boat and they allow you to hoist the sails with the crew! Not a very wordy tour they told you a little about the boat and the parts of the boat and allowed you to enjoy the view. Got a coupon of Groupon and it was very affordable! Would recommend. read more

Tall Ship Windy - Skyline at night - Boating Near Me - Chicago, Illinois

See all

I have been on quite a few sailing ship tours and this was one of the best. Our crew were professional, friendly and worked well together. Nick was the storyteller and his repertoire was delightful. It helped that we had the perfect sunny day for smooth sailing. I will always choose a sailboat over a motorized vehicle and this was delightful read more

The views of downtown Chicago & its skyline were beautiful! The sailboat was quiet and very smooth! The crew was fun, especially Matt, he was very good at telling us about Chicago! 08/13/20237 read more

I feel scammed by this company. They charged an additional $9.20 for the tickets (2). The tickets used to be valid until September. These expired just a few weeks into the summer which was June 15th. They did not mention that the ship is a minimal replica of a real Tall Ship. It is nothing like the Tall Ships that originally came to the Pier. They mostly stayed close to the pier and didn't go out to the main part of the lake until the end of the trip. Very disappointing. The only positive was a very nice crew. read more

They treated us like friends. I brought my husband, my friend and her son. They made sure her son got to experience everything hands on and made him feel special. His mother couldn't thank us enough for bringing them and the ride was so relaxing and informative! read more

Tall Ship Windy - Sails, skyline - Boating Near Me - Chicago, Illinois

DO NOT, DO NOT, DO NOT PURCHASE FROM HERE!!! Purchased tickets here during the day for fireworks cruise, the weather took a drastic turn it was obvious you couldn't view any fireworks. They would not let us have our money back even though their next fireworks cruise was Saturday well after we fly out of town. STAY AWAY! Especially from the nasty wide woman. read more

What a fabulous time! I will most Definitely be going again. Both kid and adult friendly.

Spectacular experience! Wonderful & fun crew, super time sailing, gorgeous sites of the lake & city and great history of Chicago!

We had a tremendously enjoyable late night fireworks cruise with our family. Purchasing drink tix ahead was helpful. VIP seating was beneficial. A fantastic view of the shoreline and fireworks. We will definitely do it again!! read more

Ahoy Mateys! Right on Navy Pier is a pirate ship, but that ship is a boat ride themed to pirates. It's quite an enjoyable experience. There are different times which are for different things to learn. I went on the boat ride for architecture. Also, the captains of the boat will ask for volunteers to raise the flags! Also, I never knew some stuff the captain said. It was very interesting. The views are fantastic. You can see a lot of what Chicago has from the boat! Don't forget that there is a bar on the ship! The captain was really good. He had a nice presentation, and had a great speaking voice! Plus, he felt like a pirate! All in all, great boat ride that you shouldn't miss! I will come back soon. read more

Tall Ship Windy - The view of some of Chicago's buildings. Fantastic! - Boating Near Me - Chicago, Illinois

Take it from me: Don't wear a skirt. Other than that, a fun experience. Great views of the city. Even better views if you wear a skirt. read more

We embarked on a Saturday 7 pm cruise aboard the Windy and after having read some of the other reviews, I didn't know quite what to expect. So I'm happy to report that it turned out to be a fun and relaxing sail on a beautiful summer evening. When I saw the crew dressed as pirates I thought, oh no, is this going to involve audience participation? But it didn't. Your cruise can be as interactive as you want it to be. You can kick back and relax on the upper decks and you'll be left alone or you if you want a little more action, you can sit on the center deck and listen to the pirates tell and act out stories. They also let kids help raise the sails (which I can imagine would be a cool experience for any kid). For those reviewers who found it underwhelming, lighten up! It's a sail boat, not a speed boat. And it's sailing not a roller coaster ride. Cruise time of an hour was perfect and we went out as far as the Chicago Harbor lighthouse, enjoyed beautiful sunset views of the Chicago skyline, and even picked up a lovely breeze. Crew was very friendly--a guy named Orion was the star of the boat and there were a few young, charming Irish lads here from Ireland for the summer to work on the Windy and one of its sister boats the Red Witch. FYI, you can book the Red Witch for private parties and themed parties. Said charming Irish lads will dress up as pirates if you want them to--I know because I asked! Arrrrrr! I'm glad I got the Groupon for $18 because I definitely wouldn't have wanted to pay the regular price of $35 for this cruise. Non-prime time tickets for sailings before 3:15 pm are cheaper at $24. If you go, I'd recommend going in the daytime so you can actually see the lake and other scenery. If you're looking for something on the lighter and more casual side, versus a textbook architectural tour, you'll enjoy the Windy. read more

A great activity for all especially with kids. It is the only boat with the masts/sails out of all touring boats along the navy pier. Pick a nice day and come out sailing.... It was spacious on the ship. There were plenty seats on the bench or on the top of huge wood storage boxes. There is an open area for the captain which was super cool as we could watch how the captain maneuver the ship. The staff on the ship was energetic and friendly. My son was excited when they asked his help to raise up the pirate flags. Shortly after we left the pier shortly, the captain ordered the staff and kids raise up the massive sails. That was really thrilling part for old or young kids. The ship didn't sail too far to the south side of the lake from the pier, not even the museum park. We were facing the gorgeous view of Chicago skyscrapers from the lake. While a pretty pirate gave us the history of Chicago and funny stories, I was just enjoying the breathtaking view. It was a bit cool on the ship as it was in mid of 70f. One of the pirates was so kind to get some blankets for us to keep us warm. The captain actually invited one boy to take the control of the big wheel for a few minutes. Very cool. Before we realized it, the ship was approaching back to the Navy Pier. We all loved the tour. It is different that the Chicago river one which you will see lots of buildings and hear the stories about this. It is more kids friendly with a great view from the lake. I have got the Groupon so it is half off for the adult ticket which is a great deal. read more

Wow, upon reading some of the negative reviews we ALMOST didn't go yesterday, luckily I decided to overlook it & went anyway... The outcome: We had so much FUN!!! It was GREAT!!!! Our host/Pirate was named Orion & I can't praise this guy enough! He knew all the historical facts & really truly seemed to love what he was doing. With a wonderful mix of humor, history, a fantastic sail boat ride & the gorgeous Chicago skyline it made for a perfect & worth while outing. I would also like to mention that the crew was helpful, courteous & extremely friendly. We got to raise the sails, there were PLENTY of seats, they provided blankets & everyone seemed to be having a blast! I can't wait till next spring to go back again!!!! I WOULD 100% RECOMMEND THE TALL SHIP WINDY!!!!!! :) read more

See all

[insert the obligatory "I'm on a boat" joke. Except you are not on a boat. You are on a ship. A tall one. One that has pirates?] Sailed the high seas (cough lake michigan) for a professional event, so I can't comment on their normal pricing or themed adventures. But I can tell you that when its a beautiful Chicago summer evening, there is no better place to view the skyline, watch the sunset, and have a few drinks than on a massive sailboat. 75minutes was the perfect time to eat, drink, and mingle. While you don't go very far from Navy Pier, that's to be expected in that time frame. And the city is breathtaking regardless. A few complaints: -we can do without the fake pirate accents. Kids like it. A boat full of female attorneys does not. -Near disaster happened when the ship did not have white wine (see "boat full of female attorneys," supra). Thankfully Bluebeard came to the rescue at the last minute. For a fresh take on an event venue, I'd check it out. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

See all

Found on Groupon while searching for things to do in Chicago. There was a decent discount. It's was enjoyable tho maybe the wind didn't cooperate completely. The crew was nice and Katie was funny. read more

All in all this was a good experience. At $40 per person it seems a little pricey, but we are always happy to support a local, family owned business. Highlights include an accommodating and entertaining staff; a full bar with great NA options for kids and the sober-curious; great views from Lake Michigan. Lowlights include an overcrowded boat, uncomfortable seating (damaged benches and various wooden boxes were used for seating); and the stench of raw sewage that I presume was from the boat bathroom and not Lake Michigan. read more

This was such a memorable experience! This was our 2nd time taking an architecture tour and we really enjoyed ourselves. I bought a Groupon for Tall Ship Windy for our anniversary. Nothing screams romance like a tour looking at the beautiful skyline! When I went to book, I realized that there was no availability the day OF our anniversary, so I emailed and asked why. It turns out they're going to be on vacation that week. I was impressed with how quickly I received a reply. Whether you have a Groupon or not, I highly recommend booking in advance. They do sell out. We arrived to Navy Pier at 3pm for a 4 tour and the 4'o clock one was already sold out. When you book, they ask you to arrive 30 minutes prior to the tour in order to board the boat. We were one of the first people in line, so we got our pick of whatever seat we wanted. We got to sit on the front of the boat (forgot what it's called) They also have restrooms and a bar. Tall Ship Windy offers different tours, including pirate ones, architectural and also a fireworks show. I really enjoyed the architectural tour. Even though I've done one with a different boating company before, I still learned some new stuff. Our tour guide was very knowledgeable and had a good sense of humor. Of the two architectural tours though, I prefer the one put on by the Chicago Architectural Foundation because you get up close to the buildings. This was still a great tour though and I loved watching them move the sails and tie the ropes. If it's hot outside, you'll really be feeling it on the boat at least until the boat starts coasting. Wear lots of sunscreen! Lucky for me, I'm always prepared so I sprayed myself a little bit extra before we took off. Final note: Please, please, PLEASE pay attention to any safety instructions they give you at the beginning of the tour. They're only giving them to you for your protection. read more

See all

I'm super mad at myself because it's been a year since my boyfriend and I sailed on the Windy, and I never reviewed it. How in the world that happened, I have no idea. So let me go ahead and start my review by saying: this tour is a blast and I would do it again in a heartbeat. Luckily, Groupon is always my way to experience new tours and fun times because it makes everything more affordable. Unfortunately, I decided to book our tour on a super cold day, so that made everything a tad less enjoyable because it was even colder on the lake. The tour itself was super fun and interesting. The tour guide we had was hilarious and super knowledgeable. I was impressed with how much she knew about the city and the history. What was a really cool aspect, is the tour was only a portion of the sail itself. They let the passengers explore the ship and take pictures for the first 20 minutes of the tour. Some aspects that really made me impressed with the hospitality of the ship was the bartender and the fact the ship was loaded with lots of blankets for the passengers. The bartender was super nice and chatty as we enjoyed some time to warm up from the cold outside. This ship is available to rent for private parties, weddings, receptions, etc. If I had a load of money, I would definitely rent this baby out and have a blast. The crew is hilarious, the ship is gorgeous, and what better than to sail on Lake Michigan and have a party? read more

See all

Had a great time! Relaxing ride while seeing the sites of Chicago. Highly recommend.

Thanks to Dana Z's review I did not wear a skirt. Phew.... Anyway, I had a great time on this. There was definitely a noticeable split between kids and adults. There is a beer stand right across from the entrance which is nice. The fact that they get customer participation in hoisting the sails is a pretty cool move. It was a fun activity to do off of navy pier. And since I got a groupon for it, it was rather inexpensive. Great views of the city. Good photo ops on a large sail boat. A great place to go with the family. read more

Overall fun experience, great views of Lake Michigan and the city of Chicago. I didn't like the fact their were no actual seats and you just sit anywhere. With covid just ending I was nervous with the full capacity boat. People were too close for comfort for me. read more

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 read more

See all

Great times! Some of the best views of chicago. Do it twice a day and a night tour. I get this every year from groupon. read more

Tall Ship Windy - Beautiful day out on lake Michigan! - Boating Near Me - Chicago, Illinois

See all