I've lived in Chicagoland all my life, but today I played tourist along with my college aged daughter & her boyfriend. We all learned a lot about our beautiful city. The ship was clean & well kept. The crew was friendly, funny & knowledgable. The view amazing (of course). I just wish the tour was longer so we could learn about points North of Navy Pier. It was a perfect day on the water. read more

Outstanding trip with pirates! We took 7:15pm tour, so we saw the sunset too. Pirate Mike was very enjoying and fun. Lots of jokes and cool stories. We had a great Sunday evening. Thank you Tall Ship Windy! The trip costed me $54 + $14 for drinks($20 value). We purchased adult tickets online via Groupon, so we saved $16 + $6 on drinks. $22 total savings - Good deal! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Having done the architecture tour on the river already, I wasn't sure what to expect from this one. But it was very interesting because he was able to discuss buildings that are not visible from the river, so I learned a lot. Our guide, Zach, was very knowledgeable and friendly, as was the crew. You can help raise the sails if you'd like. There is a cash bar, although I didn't use it. I would definitely recommend this if you are looking to get out on the water and see the gorgeous Chicago skyline. read more

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. read more

My friend bought 4 tickets on Groupon so that we could both take our daughters for my child's 4th birthday. We had a GREAT time! Got there on a Saturday morning just before a storm rolled in, so they informed us that we'd have to wait until the ride at noon. We killed a little time on the pier and headed back for a great voyage! Our girls really enjoyed themselves as did my friend and I. The crew were wonderful. We got to ride on the pirate cruise and enjoy the stories told by Alex and Patrick. We ventured up to the foredeck and aftdeck with the kids and chatted with the crew up there. Everyone was so friendly and excited to explain things and show us anything of interest. We had a great time and I would definitely recommend it to a friend! read more

Great day on a hot afternoon. The crew was friendly and entertaining. They involved the children to host the sails. They were teaching us about sailing at the same time. I would recommend this to anyone whom has never been on a sailboat and wondered what our might be like. read more

We went on two cruises last week. My 20-something son and I enjoyed them fully. The first cruise was delayed for 45 minutes due to bad weather. A docent entertained us for that time with information about living on the ship, different places the ship had been, and unusual bits of information. Once we could set sail, it was lovely. The second cruise was the Aaarghitecture tour which I enjoyed because the docent had many interesting tidbits about Chicago that I had never heard before. That was refreshing (as was the breeze) because I've gone a 2 other tours of the city on past trips. I found the staff to be very pleasant and well-informed. CONS: We made our registrations online and later found a 2 for 1 coupon in a magazine which we unfortunately couldn't use. Snacks were skimpy and expensive - but that wasn't unexpected. read more

This is the best deal of the ships operating on Navy Pier, and a great attraction to take the family to when they're visiting. I would highly recommend a trip after about 2pm or so, though, in order to avoid the terrible throngs of school children that often function as under-impressed, sulky moral vampires. This probably goes for just about any kind of public attraction, but its especially true when the story-tellers are trying to get a group engages with an audience that would rather snicker at the word 'spanker' and refuse to get excited about or involved in anything. The wait wasn't long at all, and once aboard the crew allows the riders to get engage by raising the sails, and a little physical activity always helps as a bonding experience to make things friendly and comfortable. From there, you're allowed to hang out and just enjoy the view or the amazing feeling of the wind in the sails, or go down and enjoy the bar, or listen to the different story sessions. I actually really appreciated how informal the setting felt - during one story, the story-teller and a crew-hand got into a disagreement about what type of tall ship sails are better that resulted in them both drawing knives and trying to use the ropes to get at each other. It was all for fun, and even though it made the story-teller lose his place in the story, a friendly dispute involving knives always makes things feel more authentic piratey experience! :D The crew is friendly, funny, playful, and helpful. The story-tellers, particularly Red Beard, seems to have an earnestly deep interest in the history of Chicago, sailing, and the great lake region and thoroughly enjoy the job. Captain "Full-Sail" Roger is also a very, very knowledgeable captain with decades of experiences and a great story-teller in himself. Though he was in plain civilian clothes, when crossed at sea he's known to turn the ship back around after the offending vessel and begin to bellow loudly for his crew to prepare to fire the (working) canons! Every trip I take on the Windy has some sort of fun incident occur! Of course a groupon deal will always make it better, but $30 for the 75ish min trip is completely worth it, and a better deal than other, lamer ships when you can have such a neat sailing experience on a sea-worthy vessel with a rich history. read more

Went last weekend with my husband's family. I'm not a huge fan of being outdoors for extended periods of time, but the guide (Dave?) won me over with his great narration as we sailed around the lake. He was not only knowledgeable about the history and background of the architecture on the Chicago skyline, he was humorous and entertaining as well. Well, done, Windy crew! read more

I've done the pirate sail twice, when I've had out of town guests with kids, and it's fantastic! The sailing itself is peaceful and beautiful. They let guests help raise the sails and learn some terminology, which was fun. The pirate stories on mid-deck were great, our storyteller was really into it and told tons of jokes. The kids really appreciated the stories, and they kept me entertained too. My niece even got to fire the cannon - that has been the highlight of her entire Chicago trip so far! This sail is fairly priced (especially the kids' pricing!) and a nice outing for visiting guests. I'll do it again when I next have visitors! read more

It was a blast! My boyfriend and I went for the 7:15pm sail (pirates edition). The staff would great! We also got to see a beautiful sunset, would go again in the future! read more

Bruce the guy who answers the phone when you call with questions and the owner is an asshole.

Our party of 6 (ages 4-64) had a wonderful, albeit hot, pirate sailing aboard the Windy. Horns did a great job regaling the stories of pirate days past! Every staff member aboard was un-pirately friendly. read more

Very fun adventure. Ship is awesome. The staff was great. The experience overall all was really good. My only complaint was i think a couple of the staff must have been in a new relationship and they were pretty touchy feely. Nothing inappropriate just bkind of annoying. The pirate that hosted was phenomenal, and hilarious. read more

Just wanted to give a shout out to these guys: they are arghhh-mazing at what they do! We had a group of 50 two to five year olds on a pirate adventure and it was SO MUCH FUN! The actors were funny, smart, very entertaining and absolutely age appropriate. They engaged the children and kept them occupied for an hour. The captain was very polite and made sure that all the kids are safe while on board. It was a great adventure! We are definitely coming back next year! read more

Great nighttime cruise to see fireworks. Captain, Crew, and Boat experience a 5. Price a little high and the seating isn't comfortable but nothing to complain about. Wish I could give a 4 1/2. Skip the cheesy tours and ride a really cool boat. Will certainly try one of the other tours they offer next time I'm in town. read more

Great crew, fun ship, good drinks. I got to help pull up the mainsail and joke with one of the pirates. Good architecture tour as well.

This is one of the best activities at Navy Pier and possibly in the entire city. This is a real sailing vessel, and they really know how to operate it. Leaving from Navy Pier, you get out on the lake in a way no other company can claim while getting to see the beautiful skyline and get a sense of what it was like sailing on the lake 150 years ago. What's more, the crew clearly gets real joy from what they do, and they're eager to give the best experience possible to the passengers, including them even in raising the sails. For those who are interested in a more relaxing ride, the bar has several great options as well. Absolutely worth the price of admission and absolutely worth doing again and again. read more

I rode this trip on my recent trip to Chicago -- we used the Go Chicago card (which we found to be a great deal btw) and this "tour/ride" was included as part of the Go Chicago package. It had a high monetary value ($30 each) so i based it off of that and my family and I gave it a try. SHORT VERSION: Not really worth it...at least for the 4pm tour, as the subject matter wasn't all that interesting and it wasn't for us. 2 options on the $30 boat ride: Sunbathe/chill on the sides of the boat (which could be done on other, nicer venues for the similar cost) or listen to the lecturer's stories (which....were not presented in a way that satisfied a $30 value, in my opinion) LONG, DETAILED VERSION: It was a busy Sunday in July, and we rode the 4pm "Chicago Lighthouse Sail: Guardians of the Harbor." I wasn't sure what i was expecting at this point, as all i knew was this was going to be a ship with large sails that we would take into Lake Michigan, and the "pirate-crew" of the ship would be providing some sort of entertainment on the ride -- which happened to be about lighthouses for the 4pm slot. We get on the boat, and its off to a good start -- the pirate theme for the employees is in full swing, and the pirate crew is yelling random pirate sayings around the deck, proceeding to ask for volunteers to raise the sails (mostly young kids, but some adults participated in this too). .....and then the trip takes a turn. Sure we are now in the middle of lake michigan, and the view is beautiful, but the pirate theme goes away and has no relevance for the rest of the tour. Let me preface the rest of the review with this: the tour guide does not MAKE you listen to his stories....you can just go to the sides of the boat and sightsee and/or sunbathe etc....but i felt that kind of experience could be done on some other, nicer venue for the same price. --- Spirit Cruises next to them offered a lunch cruise on a bigger, nicer boat for $35. Now, one "pirate" is talking to us for the rest of the ride, or...should i say "lecturing" us? He describes various stories about the lighthouses and their historical significance, a dog named "Sport," and other various tales involving determined lighthouse keepers, the creation of the Michigan pier, and the like.... So yes, I learned something. BUT -- it was more like a college classroom style instruction rather than an entertaining one. You know how you feel in class when the professor truly knows what he's talking about, and you respect that, but he just doesn't present it in a way that interests you? Poor fella, unfortunately, that's how i felt. He lacked a microphone, so it was hard for us to hear. The stories, other than one about how they changed the light in the lighthouses (where a show and tell of the light was thrown around the audience) lacked visuals...or they functionally did.....He would occasionally show us a black and white picture about 3"x5" in a 1" ring binder.....(How all 100 of us on the boat were supposed to see that, i'm not sure.........) I was sitting in the middle of the boat..in the same place as the presenter, so I was able to see all this, but i can only wonder the experience of those of the front and back of the boat (bow and stern/aft)....:P They probably got a good tan! Tall Ship Windy --- if you are reading this, this is my critique for you: Please make the pictures larger or make handouts or something if you are going to show people pictures during a lecture. Second, add microphones and speakers so everyone can hear. Third, background music would add to the environment -- since the speaker has a mostly scripted speech anyway, perhaps music timed to that speech would make the speech more interesting. read more

Cruise was beautiful and provided great photo ops of the skyline. Crew was funny and most importantly kept everyone safe.

The crew was fun!! Loved the ride. We went down for the Wednesday fireworks. It was so worth it! It is a family owned operation. There is a nice little bar on the deck. Planning to go to one of their amazing theme events next! read more

An amazing experience! We went to the Wednesday night fireworks sail and it was the HIGHLIGHT of our entire vacation. Relaxing and entertaining with an amazing view! read more

An enjoyable experience. My girlfriend and I went on the architecture boat tour, and while it wasn't a full architecture tour -- we were splitting our trip with the pirate tour -- it was fun nonetheless. read more

A must do if visiting Chi-Town with the family and kiddos. My son was able to man the sails with the crew,learn alot about sailing and sailors,shoot of the canon and see Gary IN across Lake Michigan. Awesome Time and there's even a bar on board! read more

The weather was perfect and it started on time. It was just too hot the way the 'pirates' were dressed, they really could dress lighter in the heat we've had all summer. Everything was good until one of the pirate girls seemed to be staring me down for a long time intentionally. I was confused because I didn't know where it was coming from but I just ignored it. Leaving the ship she looked at me again, and whispered something to the guy next to her which I could just tell was about me. Talk about awkward. I had a good experience, but there's a 99% chance I won't be getting back on it. They let too many people on the boat to the point that you can barely move around. People would be sitting on the floor. read more

This rating is not for the experience. It's for the fact that they charge $10 for a baby to board. I have never been to an attraction that charges for a child under 2. I find it ridiculous. I'm still contemplating whether I want to pay. Will definitely update the post if I do. read more

We just did the pirate cruise today, 2 adults, 5 kids under 8! We all had a fantastic time. The kids were completely enthralled with Austin's great story telling. The crew were very friendly and you could tell they loved their jobs! Great way to enjoy the skyline of Chicago while aboard a beautiful tall ship. Highly recommend. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

What a great time we had! The crew were very welcoming and told some great pirate stories. Totally recommend you take time to sail with Tall Windy. read more

Four and a half stars. Great time. I wish we had a longer tour than the one-hour. I've had boat rides before, but this was great with the raised sails and the wind pulling us. Staff was friendly, but not overbearing. A few riders volunteered to pull the lines and raise the sails, but it seemed kinda for show, as the staff raised the other sails by themselves. There was a lecture on sailing on the Great Lakes that was very informative, but if you didn't want that, you could stay in the bow or stern and take in the view of the world's most majestic skyline. read more

What a great way to top off a busy, stressful week at work!! Sailing on the Tall Ship Windy has always been so much fun for my boyfriend and I. We have gone a few times, but this time, went for Aaron Wilhoft's special show on the Ship. What a great artist, and it's an amazing mood and ambiance that it sets - there's nothing better than a warm night out on the water, with great acoustics and song from an amazing singer/song-writer... If you haven't gone out on the Tall Ships yet, you have got to go. It is a unique way to see the city and enjoy a beautiful night in the summer. Thanks for a great time! read more

I'd like to start off my saying that tall ship windy is perfect for people with children. Not only does it offer the classic architecture tour, it also offers themed events. The name of the tour I went on was something like "real pirates". An employee dressed up like a pirate told stories on the main deck. People not interested on the stories were able to go onto one of the upper decks to relax. read more

From start to finish the captain and crew make this an awesome experience! Crewman Dave was exceptional with the kids, he taught them knots to tie, told true stories of piracy on Lake Michigan from 150 years ago, and shared cool stuff from his treasure chest. I can't recommend them enough for a fun family adventure. read more

Awesome girls' day out!! Birthday girl had a lot of fun!!!! Great fun crew. Thank you.

Last night we took our first trip on the Tall Ship Windy! I must say it was truly a treat and totally worth the money. It was such a great way to see the beautiful city of Chicago! I've been on many types of boats on Lake Michigan -- but this was my favorite ride #tallshipwindy They have a great staff! Splice was an excellent storyteller, funny and very articulate. We enjoyed listening to his Pirate stories. It was a wonderful evening! The boat is perfect, clean and peaceful as you set sail across Lake Michigan. Navy Pier - Lake Michigan Lakefront Chicago. I will definitely go back with friends and family. I loved the sunset view behind my favorite city -- Chicago. read more

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We did a late afternoon architectural tour and my teenagers loved it. Relaxing cruise and Andrew did a great job talking about the history of Chicago. read more

We had a wonderful sail yesterday on the pirate ship! We went for my husband's birthday with out 1.5 year old. The sail was just long enough that our son didn't get too fussy until the end. He really enjoyed being out on the water. My husband and I loved the two stories that were told on our sail. It didn't hurt that it was absolutely beautiful out on the lake. A suggestion to those going, have your tickets, don't just show your phone. It will help keep the line moving. Also, pay attention to others, there are up to 150 guests on the ship, be considerate to everyone, we all want to enjoy the sail. read more

Fun time. Our kids really enjoyed the pirate tales cruise. The overall experience is good. Wind was calm on our cruise so not as much sailing as I'd expect. read more

We sailed on the Tall Ship Windy during the tall ships festival. Our sail was wonderful because the crew included us at each stage. Volunteers were asked to help hoist and lower the sails, and one person even got to fire the cannon! The crew was full of info, tall tales and fun stories about the ship and Lake Michigan. Save up and make this a fun family event! (Unfortunately $$, but the ticket price helps pay for the excellent crew who make the experience memorable) read more

Great fun ride. Lovely knowledgable crew. It was quite spectacular and worth every cent.

I went on Windy last thursday and it was awesome! The crew is very nice and knowledgeable and the ride was just so beautiful. Windy is definitely the coolest ship out there on Navy Pier!! I highly recommend. read more