We had a good time out on the boat. Fun to get to help set up the ship and learned some cool facts about pirates on Lake Michigan and Dan Seavy! Andy the kid was super cool and made the trip much more engaging! read more

Tall Ship Windy - Shooting the cannon - Boating Near Me - Chicago, Illinois

These were the best fireworks I have ever scene. Crew were very attentive and careful. I get safe.

The music during the fireworks was way too loud and annoying. The staff did not feel welcoming.

My mother and I were visiting for the weekend and decided to get the Go City Pass and as part of the 5 venue pass, we chose to go on the Tall Ship Windy and I am glad we did. Turns it this is the only family owned and operated business at Navy Pier - so go support them now!!! This is also one of the only 4 mast post ships in operation in the United States so how cool is that! The views are amazing, the staff super friendly and knowledgeable, there's a bathroom and bar on board and they have fun drink names and you can pay with cash or credit. Oh and hey use BAMBOO STRAWS from a woman owned business!! Holler!!! Adam was a great bartender and Nick, our storyteller was awesome! I love when the staff is knowledgeable and personable...it makes the experience so much better!!! While on the cruise, you get to help raise the sails - so super cool!! And they tell stories is pirates on Lake Michigan. Fascinating stories all around!!! If you want to do a boat tour while in Chicago, I would definitely suggest this one!!! read more

July 2021 - COVID Review: My husband and I rode on Tall Ship Windy as a part of our GO City Pass. It was a great and more chill experience and I'm glad we saved it as our last ride on the water. It's not like those other Chicago boat rides that actually give you a tour and talk to you the whole time. This ship takes you out on the river so that you can enjoy the scenery and relax. They also have a bar on board where you can buy alcoholic and non-alcoholic drinks and snacks! The staff were great and you can tell that they really enjoy their jobs. Get in line at least 30 minutes early and even earlier if you want better seating! There's no "true" seats so do be mindful of where you sit if you easily get seasick or can be worried about slipping. Highly recommended experience for your time in Chicago! read more

Wow!!! My wife and I have been wanting to try this for years and being a Southside Chicagoan we finally did. It was an AMAZING sail and the staff was Friendly, Loved their job, and Knowledgeable. Talked with other passengers and made new friends. Saw Chicago sunset skyline so Beautiful. Guys take your mate and they will love it! We will definitely be back. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

For a family owned establishment, I say they are doing things right. Sailing, to me, is quiet, the sound of the water and wind, not pirate music or any other music to be honest. My only suggestion is to stop playing music all together. I would have personally gave 5 stars without it. Staff was eager and enthusiastic. read more

The Sunset Lake Michigan cruise was a great experience. It's markedly different from Chicago boat tour companies, as it's more of an relaxed vibe with Old-Timey music in the background. There isn't much that happens beyond that, it's more about the boat ride and experiencing the Chicago Skylinr from the Lake. Overall I would recommend as another activity to enjoy during your trip to Chicago. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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What a great way to break up your time in the city. I really enjoyed spending time on the ship, and especially while we were just being whisked along by the wind. A fantastic view of the city from the lake was spectacular. The crew were fun, the bar was OPEN!!! (bring a mask) and luckily for us the weather was fabulous. You really want it to go on.. and on for much longer. I found the serene peace was the perfect contrast to the hustle of the city and a great way to spend some time unwinding. Great fun! read more

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I would give half a star or no star at all if I could - the Sunday "Special Event" 2023 Air and Water Show was anything but special. Apparently the new owners couldn't bring themselves to actually putting the ship in position to watch the entire Air and Water Show - it was the ultimate bait and switch as the ship was back at the dock before the premier event performers, the Thunderbirds, even appeared. Members of the crew just lounged around taking up limited seating space at the bow and being in the way when it came time for limited photo opportunities due largely to the fact we were light years from the activity except for the moments when some military jets made wide turns far out in the lake. As for sailing, due to no wind, it was a joke and being a sailor, they should never even attempted to raise them - they just got in the way of viewing the show. Given the heat, they could have slowly motored to create a little apparent wind - perhaps that's how they make the bulk of their money, off of the bar, while baking everyone on board to death. I had done the Air and Water Show on Windy 2 years ago and it was a 10 star trip despite wearing a mask during boarding for Covid and some anchoring woes. In 2021 the ship left Navy Pier early enough to be on location prior to the start of the show and they stayed through to the end. It wasn't until after the show that the sails were even raised so viewing the airshow wouldn't be restricted. I had driven over from Michigan for this event, and thankfully watched the Saturday show from the lakefront. Audio of the show broadcast on the boat was haphazard at best due to the time delay from WBBM - we listened to far more commercials and traffic reports than we did air show commentary. The crew should have just turned off the feed and put on some music. Never again on Windy - a total bust in terms of value and disingenuous to hype it as a way to see the show. Heading back in before the premier performers even appeared was the nail in the coffin for me. The attached photo is NOT from the ship, although it should have been read more

Tall Ship Windy - Had the cruise actually been as advertised, we SHOULD have seen this! - Boating Near Me - Chicago, Illinois

The entire experience was fun. Great crew and guide. Interacted with us . Great experience to be on a schooner and watch and/or help hoist the sails. Passengers are free to walk around or sit. Tour guide was super. Highly recommend. read more

I highly recommend this affordable, fun, memorable experience to everyone. I had a great time and I cannot emphasize enough how therapeutic an hourlong sail trip can be!! I enjoyed this better than the 75 minute architectural tour through Wendella actually. I also have to shoutout the staff who were also super friendly and enthusiastic to the passengers throughout the entirety of the trip. Please consider exploring Chicago in this activity this summer! read more

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

Such a fantastic experience, will definitely do it again next time we're in Chicago. Besides the knowledgeable and friendly crew and the awe inspiring sails and rigging being out on beautiful Lake Michigan slicing through the water with only the power of the wind honestly makes me super emotional. Highly recommend. read more

Tall Ship Windy - Lake Michigan, the Chicago Skyline. - Boating Near Me - Chicago, Illinois

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Tall Ship Windy almost sailed directly into the breakwater wall. Our captain yelled "brace for impact" as we came within approx 5-8 feet of the breaker wall under sail at speed out of control in the harbor on Lake Michigan. Most of the people seemed to be unaware of the danger we were in. A female member of the crew dove/fell a cross the deck as well and appeared to be shaken up. read more

We thought this would be a great way to see the city from another view. First off it is promoted as a sunset happy hour cruise. They literally took us out and basically went around in circles. Never riding along the shore line. Not one crew member spoke about the buildings or Lake Michigan. We actually just sat pretty much just taking to each other as the boat went around in circles. For the money they charged there should of been some kind of interaction not just have a few people help put the sails up and nothing else. What a waste of money. The only positive thing I could say is that at least it was nice Pick a different boat this was the most boring thing ever. read more

The pirate pub cruise was AMAZING! Would definitely recommend and plan to go again next season.

Great crew, wonderful views of the Chicago skyline. Conveniently located at Navy Pier. Thanks for the great weather! On time departure. Highly recommend! read more

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Ok so 20 of us went on the Tall Ship Windy Pirate tour. Buying the tickets was a piece of cake. We purchased them ahead of time, not at Navy Pier. The day began as a windy, cloudy cold day but it turned out to be spectacular weather for when we set sail! #lucky! We purchased drink coupons before boarding because you get a deal, $8 instead of $10. Drinks were $7-$10 on board. Anyways, we did the pirate tour, mainly because with timing and a dinner reservation we had, it made more sense. I would say overall, the pirate tour is better for kids. The crew did an awesome job making it interactive. Kids and adult guests could help raise the sails. The lead "pirate girl" did not stop talking the ENTIRE TIME...ok she stopped for maybe 10 minutes, but man talk about exhausting. I'm a teacher and I feel her pain. She stayed in character the whole time and did an awesome job. Honestly, our group didn't care about the pirate stories, but the kids seemed into it and she even got our uncle in on some of the story telling and it was hilarious! It's a nice boat ride. I get motion sick REALLY easily and I was fine, however the laze was really smooth that day. Would I go again, ehhh I don't know. I would like to do the architect tour, but like I said our group chose the pirate tour because timing worked out better for us. It was a great job by the crew, they also said its a family owned company which is always a plus :) read more

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This was an absolutely amazing experience! I'm so glad we decided to take a chance on a boat for the fireworks cruise, but even more excited that our boat was a tall ship! That's just an experience you don't see a lot these days. The crew was super friendly and approachable. They had some great history about the lake, the ship, the city, and the architecture. They also shared their Chicago wit with the rest of us, which was a nice touch. The fireworks were stupendous, especially from out on the water. I'm not sure I can see them any other way now! But, to experience this from a tall ship, a functional sailing vessel, it's just cool beyond words. I would absolutely do this again, and I highly recommend it to anyone who enjoys a quick boat trip, an amazing fireworks show, and a relaxing way to enjoy an evening down by the Navy Pier! read more

The whole crew was fantastic! Especially Andy "the kid". Fun, entertaining and made it a great sail!

Took the kids to the air and water show on August 20th 2023, horrible experience! Incredibly hot and could not see much of the air and water show as promised! $120 is way too much per ticket. Most people went below to get out of the sun and the Heat, people were getting sick and throwing up because of the heat there was no mist there were no fans there was nothing to help people stay cool. Needless to say, no one had a good time. You need to really charge less for this experience, and 3 hours is definitely too long. Horrible experience for the children and for the adults! read more

We went for the 75 minute pirates cruise aboard the Tall Ship Windy. This was by far our favorite part of our Chicago trip. We were able to help hoist the the masts and the crew did a great job getting everyone involved. The pirate stories were engaging and fun for all ages. Also the views of the Chicago skyline were amazing. read more

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Highly recommend buying tickets for Tall Ship Windy! It is a great activity for ALL ages! The staff is friendly and the captain we had was engaging with the passengers and had a great sense of humor! The 75 minute ride was the perfect amount of time and the Chicago skyline view from the lake was beautiful. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

Great time!!! Highly recommend! For kids and grown-ups. Tourists and Chicago natives as well.

we went on the sunset tour and it was amazing! The staff was friendly and the boat was clean, and we got a great view of the city! It was a real fun experience! Definitely would recommend! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Amazing!! On the list of must do in Chicago! Especially the crew, great to watch them work and set sail!!! Capt All Sails Randy picked a great playlist for our sunset sail! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

Great experience, entertaining crew. magnificent views of the skyline. Only negative: I wish there were no music so we could have enjoyed the quietness of the boat bobbing on the water. read more

Terrible customer service. We were delayed 2 minutes due to all the Lollapalooza traffic and missed the boat. No big deal, we definitely don't expect the boat to wait for us. We asked if we could pay to upgrade to the next trip ($10 more per ticket) or if we could just go another day since we paid and none the trips have been sold out so there's space. No, no refunds, no exchanges, no help, you can buy another ticket full price. I just asked since we already paid full price and it wouldn't cost them any extra since none of the trips are sold out and they simply don't care. The first attendant at the window seemed reasonable and asked the manager who categorically refused any type of assistance. I again explained that this seemed like very poor customer service since we bought two full price tickets and we've received nothing in return. The company has not lost any money and my requests would not cause the company to lose any money either. In fact, if you approved charging me the extra $10/ticket for the late trip, the company would make MORE money. She just said no. This is our policy. We don't offer anything. You can buy a new ticket at full price. Unless they start exhibiting better customer service, I would never recommend anyone to pay for this trip and I will not buy any more tickets. Thanks for absolutely nothing. read more

The night we had a cruise planned there was a torrential rain 1 hour before we were to set sail...the city flooded and we couldn't access the pier on foot. Company was VERY difficult to work with in getting information on how to deal with the situation. They told us they would refund anyone who couldn't make it to the boat in time but getting those refunds took a lot of work and several in our large party had to file disputes with our credit card companies. Those who made the cruise said it was not worth the money ($82/ticket)...the boat was empty and they still ran out of rain ponchos...fireworks were 10 minutes and just so/so...nothing special. Don't waste your money! read more

The crew and Captain Ralph were great! Beautiful city! Great information on the city! Would do it again! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Do not try to work with Tall Ships WIndy! I had purchased a Go City pass for my family on our vacation to Chicago. The children were very excited for the Pirate Sail but no, the young man at the ticket booth refused to accept the Go City passes. I tried several times to show the Tall Ship WIndy listing on our choice of Chicago adventures, but no, I was told I had to purchase the tickets. Too bad for the employees working the cruise. There were lots of open seats for that sail and the crew missed a hefty tip. Thank the ticket booth kid. read more

Just got off the boat not that long ago and I highly recommend this to anybody in the Chicago area. The crew is very eccentric and genuinely enjoy what they do and the sites you'll see out on the water are breathtaking, from the city skyline to the wonderful sunset we just saw. Our guide kept the tour very entertaining and I felt like the jungle Cruise at Disneyland again ha ha. Great tour and highly worth it. read more

I'll be 100% honest I was so skeptical when my mom booked this. Upon arriving they take your photo and start the introduction. It was totally incredible experience with the captain and or favorite girl Shark. Captain Bruce was definitely aware of the wind and the crazy direction changes such a smooth ride and a miraculous view of the skyline. Definitely will tell everyone to put them on the itinerary when you visit Chicago read more

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I came here for a charity event that I was on the board for. After months of planning, the day had finally arrive and we were so excited to sail on this ship because we heard so many great things about it. The staff were super nice and very attentive. They gave opportunities to have our guests raise the sails and help make the ship sea worthy. But also shoot from the cannon if they donated $100 to our foundation. The cannon was certainly popular. In our agreement, they allowed us to have all wine and beer on board free and even assisted us during our auction. Music and lights helped set the mood. What was really amazing were the awesome sunset views and views of the city at night! We chose the perfect time to sail. All through the event, the guests seemed to really enjoy themselves. Thank you so much Tall Ship Windy for an fantastic night! read more

Loved every minute of this 75 min boat ride, we got our tickets off Groupon and received drink tickets which was a nice plus. Shark gave a lot of great information on the city's history and the architecture we see today. My daughter loved raising the sails. We would definitely do it again. I highly recommend if your looking for something different and fun to do in the city. read more

Tall Ship Windy - View from the sailboat of the skyline. - Boating Near Me - Chicago, Illinois

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

This review is going to center around the topic of CHEESE... no you wouldn't have guessed that there is a relation between cheese and a sailing tour on Lake Michigan---but there is. Indulge me. So my head is made of swiss cheese, because I have already closed my Chicago adventures chapter, and am now happily and giddily on my Portland perfect one, reliving all of the awesome things that I love about Portland (just today, buddy in CO and I were saying how much we both mised Portland, as we met one another there). Woops! I actually forgot to review one of the highlights of my time there: sailing on Lake Michigan on that crazy-looking pirate schooner thing that fired a fake cannon.. twice (there was a bachelorette on board). Secondly, the two hosts aboard the ship, who kept us passengers entertained and guffawing often were a couple of cheese balls (and I'm not referring to the kind in the Planter's canister either). I happen to get along royally with cheese balls, and at times have an uncanny resemblance to one myself. Their jokes and their timing, their energy was quick-paced, as was their wit and charm. We learned everything from some IL folklore to a few pirate stories, to the architectural history of Chicago's skyline. Granted, there was a binder as a visual aid for the dude who was in charge of the history portion and I was only saddened that we didn't sail further out into the lake itself. For a tad over an hour in duration, we only got as far as beyond the breakers, and spotted Gary, IN (Jacksons) and I seem to recall that's when it took a 180, and headed back to the Navy Pier. I like Erin K's quip about there being an exp. date on an experience. i still recall many things regarding this tour (though it occurred in May) like the crazy rainstorm that occurred just a few hours before, and no one knew whether there a tour and a sailing was going to materialize disappear for the day. I recall getting some Garrett's popcorn while in the no-man's land of waiting for Mother Nature to be less fickle! Overall, TSW is a safe and family-fun way to enjoy a very mellow sail. The stories are entertaining and the guys are hams--ahem. I mean, they are *cheese balls* (no I'm not going to move from cheese to porcine). Great ship; majestic and very regal in the water. Would come back and take another themed tour, as there are several to choose from. besides this format of being on the water itself in Navy Pier, there is also a fancy cruise dining giant, and also a passengered jetboat-type excursion. read more

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As new Chicago residents, when we have friends and family come and visit, we like to do unique things with them. The Tall Ship Windy is an example of that. It's not your typical Chicago boat tour, as it's a super unique boat that instills a sort of "Pirates of the Caribbean" vibe. Boarding process was simple. Boat rules obvious. And the crew were inviting and non-pretrntious. Bar on board was cheap, and the selection acceptable. The only reason I didn't give this tour five stars was because of the Architecture information given by Sarah. Don't get me wrong, the information was accurate, but the way in which it was communicated was, well, kind of laborious to listen to. Sarah, if you are reading this, please don't be offended, we really did enjoy the tour. There were three primary issues that if you guys worked on, would make the cruise perfect. No joke. 1.) You sound out of breath the entire time. Like you're running on a treadmill while talking. It was super confusing and massively distracting as the words would sometimes come out fast and mumbled. 2.) You say the word "Umm" an unbelievable amount while presenting. As a public speaker myself, I recognize that this is VERY normal. But with a little bit of practice, this is an easy fix, and it will add so much more professionalism to the presentation. If you made it a drinking game on the other hand, it could be tons of fun. Haha. 3.) Durring the first 10 minutes of the tour, we legitimately could not hear anything you were saying because the crew on the front of the boat kept interrupting our listening to tell us rules and give us additional boat safety info. That's totally fine, but maybe this should be done at the beginning of the trip, before you start your presentation, rather than durring the presentation. It takes so much away from the experience when you can't hear info you want to hear. It's definately frustrating. Overall, it was a great trip. We will totally do it again with other friends and family who come to town. So take this review as a positive critique rather than a negative one. Thanks for a great day on the water guys! We really appreciate the uniqueness of the Tall Ship Windy experience.I read more

Tall Ship Windy - Gorgeous views from a super cool boat. - Boating Near Me - Chicago, Illinois

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

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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