BEST thing to do in Chicago. I am a local my whole life and shame on me for not doing this sooner! What a wonderful experience. If you have kids, the pirate cruse is a MUST do. A lovely, relaxing boat that entertained my daughter--from hoisting sails to pirate tales! I was able to actually enjoy some downtime while the awesome crew regaled her with adorable pirate tales. Such a treat. Lovely boat with knowledgeable, experienced crew. AND, there is a Groupon to boot. Don't miss this. read more

Live theater aboard ship - what's not to like? What caliber of actors (singing no less) can be got to do that....we weren't sure, but were pleasantly surprised at how funny they made it, with some fine voices among them, and just the right amount of audience participation. The lucky part was incredible weather. Hope Windy does more like this! PS to Brian G: Is it fair to write such a mean-spirited review because of flies? read more

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Saw the Groupon while visiting Chicago and decided to buy it. The cruise was worthwhile. We took the Real Pirates cruise, and Captain Crossbones was very entertaining. Really funny guy and the kids on the cruise really enjoyed his antics. The cruise itself was smooth and we got to see the Chicago skyline from the lake. It was beautiful. However, I would have liked for the boat to go out on the water a bit further. Otherwise, nice cruise! read more

Tall Ship Windy - Chicago. - Boating Near Me - Chicago, Illinois

This was one of the biggest highlights of my trip to Chicago and when I make it back, there is no doubt in my mind I will be back. When I was there I got the Go Chicago Card and it was included. Just a breathtaking view of the coastlines and if you love ships (or a history geek) like me, this is a must! Windy is a beautiful 4 masted tall ship which actually does run solely on the strength of the wind (unless the wind isn't blowing strong) and gives you an amazing view of the coastline. For the history geeks, stay on the main deck and chat up with the hilarious Redbeard. For ours, he brought out a big box of random things used on a ship and had the crowd guess what the heck they are. He had some very hilarious stories. And if you're not into that, no worries! Get yourself a drink below decks and sit back at the bow or stern of the ship and just enjoy the view. read more

Tall Ship Windy - This is Redbeard, your hilarious and awesome guide on the tall ship Windy of Chicago - Boating Near Me - Chicago, Illinois

Great boat and a better crew. We did the 12:30 Sunday afternoon pirate themed your. Had the wife and 3 kids along (ages 5,4, and 2). The Pirates were incredibly friendly and engaging with the children. Very interesting pirate stories that kept my young ones interested. You are free to walk around this large boat...the captain was incredible as well. Friendly, knowledgable, and great with the kids. I would highly recommend this for a family with kids, you and a date, or group of friends. Full bar on the boat. read more

Tall Ship Windy - Pirate stories - Boating Near Me - Chicago, Illinois

I've done this twice now, and both times were great! I would recommend this if you love gazing at the water, the stunning Chicago skyline, and learning about the beautiful architecture. Had a fun time with the most entertaining staff that make this tour what is is!! They were awesome. read more

Captain of this ship is lucky i wasn't there.. Today,August 9th was my sisters 50th birthday. My niece was told over the phone,my nephew (in a wheelchair) would be able to board. Not only was that false,they were told to bring chair up the stairs by hand,only to find out he couldn't board because it was too narrow. Not only that,but the captain of the ship was literally yelling,in front of my nephew and customers to get off the boat. I wouldn't recommend anyone to support a stubborn unprofessional business like this. Again,he is very lucky I wasn't there read more

Lots o f fun. Perfect for a hot day on land. The cool breezes were complemented by the great Chicago stories being told by the head pirate. The crew worked beautifully together, joking and acting like pirates! Charming for all ages! read more

The crew was so friendly and helpful, the Captain was amazing and let my niece steer the vessel and even let her turn the sail boat around to head back toward Chicago. It was an amazing experience all around. Will definitely do this again if we ever come back to Chicago! It was well worth the price and we really enjoyed this experience!! Highly recommended!! read more

Tall Ship Windy - Captain letting my niece steer the vessel! - Boating Near Me - Chicago, Illinois

The crew was great. They encouraged my grandchildren to help raise the sails. During the trip they talked to the kids and explained how the boat worked. they were very knowledgeable about the city. Everyone's personality made it feel like we were sailing with friends. I truly enjoyed the the trip. read more

I've always enjoyed my trips on Windy. This was my first July 4th cruise. No pirate songs or the usual banter. No fireworks. Total lack of the usual experienc. I would not go again for a holiday event. read more

Review number 400, can you believe it? I hit my third Yelpversary last June and seriously, 400 reviews later and here I am with friends, lots of great dining experiences, parties and a sweetheart to show for it. So happily, I have a five star review to go with it too, including a fantastic day with aforementioned sweetheart on an awesome boat in a beautiful city. Commence 400! Thanks to Groupon, we had two tickets to the Tall Ship Windy and happened to pick the most perfect day on the planet to go (and had only two days left in the season, handy). 72 degrees, not a cloud in the sky, sparkling waters and a gorgeous skyline, we boarded the ship and waited to set sail. The pirate lady and gentleman were funny and entertaining while they told us some cool stories about piracy on Lake Michigan from centuries back. Thanks to our winds and skilled captain, we broke the record for fastest sail, over eight knots! The crew works on tips so be kind and fork it over, they deserve it. Windy is pricey without a deal of some kind so I would hold out and go only then, but really it's so worth it. Beats the pants off those obnoxious Seadogs any day. Happy 400, y'all! read more

"But I don't wanna be a pirate" says the Captain of the Tall Ship Windy Why the pirate theme?!? I don't know?! It's a 148-foot Schooner with just a pirate flag and nothing else (though a Schooner was a very common boat used by pirates). All of the crew except the captain is dressed up. The captain seemed like a grumpy man (at least he was that day), tired of his job and probably sick of all the kids, crew including. He didn't speak to anyone and just yelled out some things to the crew, but not in a pirate voice. I would have liked at least a "Scurvy Dog" or something to that effect belted out. What's different about this boat trip compared to the twenty others at Navy Pier?! They don't seem to care where you go on the boat! Then again, is that really a good thing?! No safety precautions, nothing. They said hold on in the beginning and get out of the way but other then that, nothing. You can crawl over things, jump, and swing. We sat at the bow (front) on the ship, trying to avoid all of the kids sitting below, being entertained by the crew with pirate stories. They must have been good because you would hear the kids squeal every once in awhile. The trip is very short at least it feels that way (normally about an hour long). However in that time it is possible to relax and enjoy the view of our beautiful city, a sense of peace falls over you (that is if you can drown out everyone). I highly recommend going during a sun set but that's probably very obvious to everyone. At $35 a pop it's not the best but be on the look out for a half priced Groupon or something. Though even still, eh, I would go on a different one. read more

This was an absolutely beautiful experience! Took my wife for the sunset sail today and she LOVED IT! We will be back.

I love the water, and I love sailboats and tall ships, so I figured this cruise would be the perfect way for us to get out on the water and learn something about Chicago. We chose the "Aaaargh-itecture" cruise that left at 10:30am, because we could learn about architecture and have some fun hearing about pirates too. We're children at heart, what can I say. I bought the tickets online the day before, when we were already at the hotel so we couldn't print them out. I wrote down our confirmation number instead - we had done that on the walking tour the previous day so I figured it would be fine. Navy Pier was further than we expected, so we arrived at about 10:20am. The line at the registration booth was about 15-20 people long. And it wasn't moving. There was only one girl working it, and apparently there was no way for someone to help her nor was there any way to help those who had already purchased. That's just poor management in my opinion. Due to this, the ship was actually late leaving, and at 10:35 they announced last call but we were still in line waiting for our tickets! I ran over to the guy who had called and explained our situation. He went to chat with the girl in the booth and announced that they would be leaving in 5 minutes no matter what. The two groups of people in front of us were using group coupons (my old foe), and apparently that took even longer to process. Even more annoying was the fact that these people were booking the NEXT ship departure time. I realize that they were there first and I don't begrudge them that - but most businesses under the circumstances would call out for those looking to board THIS departure. It's the same as letting a single through when waiting in line at a ride. But apparently not here, and we were bumped to the next departure - which was a different topic, and it meant we missed the theatre tour we had been planning on doing later. The topic was "Real Pirates of the Inland Seas". And it was completely focused on children. Okay, it's pirates, I guess we could have figured that it would be aimed to children, but the one that we had planned on would have given some information about architecture at least. The boat itself was beautiful, and the water was lovely, so we just sat and enjoyed the breeze and the views. It was peaceful, but not what we had paid for. Oh, and I should also mention...the cruise we were stuck with left at 11:45...not good for my Irish complexion on an unbelievably hot day. My souvenir was the worst sunburn I've had in a long time, and mild heat exhaustion that had us in the hotel for the rest of the day. All in all, it's probably a better tour for families - and get there early! read more

By far my favorite boat to bring people on when visiting the city. I have been on this boat about 2-3x a year for the past couple years & I enjoy it every time. Yes, I know all the stories by now but it is still fun. I've taken my siblings on the boat, grandparents, friends & even two dates ;) The setting is perfect for any occasion. You can listen to the stories or go cuddle up under the blankets they provide at the top of the boat. The boat has a cute little bar also. Every staff member I have ever met is super friendly & always smiling. I can't wait to go on the boat again this year. read more

I'm a native Chicagoan, so I don't seek out touristy stuff unless out-of-town friends or family come to visit. However, I saw a LivingSocial deal for Tall Ship Windy and I love sailing, so I figured I'd give it a try. The first time I tried to go was on a Saturday in July 2012. We wanted to do the haunted tour. When I arrived with my tickets printed and ready to go, the guy at the ticket booth was super rude and told me we couldn't go because the haunted tour takes place while Navy Pier does fireworks, and evidently it costs more to do a fireworks cruise. I tried to explain to him that I wasn't signing up for the fireworks cruise, but the haunted one but he replied with '"I have a nearly full ship of people paying full price. Why would I let you go on for half price with a LivingSocial voucher?" Thanks, jerk. After being totally turned off by the rude ticket guy, I forgot about my LivingSocial vouchers until I got an email reminder that they would be expiring soon. I decided to try a different tour, this time making sure it wasn't during fireworks. I showed up, presented my tickets to the same ticket guy, who was just as "pleasant" as last time, but thankfully this time he accepted my vouchers. We were told to show up at the boat at 7pm for a Coast Guard briefing...this took place closer to 7:20 since the crew was busy trying to get more people do go on the cruise, which bordered on creepy and inappropriate (pirate guy making sexually suggestive comments toward clearly underage girls...yeah. Not cool). Finally we boarded the boat for our Rum Runners cruise, which was supposed to be about gangsters and prohibition. The crew was very friendly and helpful, and since we only had a handful of people on our cruise, they did a great job of engaging everyone. However, because there were so few people on our cruise, I think the stories got a little informal and the storyteller just sort of casually went through the tales. On that note, I was pretty disappointed with the tales of gangsters and prohibition. The storyteller only talked for about 20ish minutes and went out of character several times. We only talked about 1 pirate/gangster, which was disappointing. I wanted to hear more! The cruise seemed really short. We didn't go far out at all. We kind of just circled the harbor and then went back. Not great. However, the view of the city at nightfall was spectacular and I got awesome pictures. Overall, I wouldn't pay full price for this cruise. Maybe my experience would have been different if there were more people on the cruise, but who knows. I will say that the crew was helpful, friendly, and mostly professional. The boat is nice, and they have blankets available in case you get cold on a night cruise. read more

I also discovered the Tall Ship Windy through Groupon, and I'm happy to say my experience was great! We did roll up on a Saturday night, hoping to get the fireworks cruise, and of course it was sold out, and there was a line of people. They put us on a waiting list, and within 20 minutes or so, we were on the boat next to those with reservations! We sat near the front, had a nice little spot to ourselves, and a great view of the fireworks. The crew that day was really awesome, funny, and laid-back. I loved that they didn't treat us like children (tours and "rides" can often get like that), and trusted us not to fall off the side of the boat without scolding or reprimanding us for sitting there. Thank you! I enjoyed it so much, that I bought two more Groupons the next time I saw an offer. My 'fella wants to try this "pirate" cruise, can't wait to see if its as corny as I'm thinking it will be... more reviews to follow! read more

We took the sunset cruise and it was such a great experience. Beautiful views of the Chicago skyline. Not a bad seat on the boat. It was a little chilly and they passed out warm cozy blankets. read more

Tall Ship Windy - Sunset cruise on Tall ship Windy, Chicago skyline. - Boating Near Me - Chicago, Illinois

We had a great time with Tall Ship Windy. We went on one of the Haunted Harbor excursions, and it was a chilly October night. The energy of the crew and cast was great, the views of the city were amazing as always, and they even had a huge supply of blankets that they offered to anyone who was chilled to the bone by the cold... of the weather, or of the ghouls? Muahahahhahaha.... Interesting fact is that the crew actually lives on the ship, but then again I am pretty gullible, so I don't know if it was a fabricated fact, or the truth. :-D read more

My wife and the grand-kids (2) bought tickets thru Group-On, although we were thinking about going anyway. I was a cold rainy day, end on May, but we chose to go (We don't get the kids often enough to be choosy). The Cruise was great (considering the weather) and everything was wet and a smaller group of people, but the "Pirate" crew whipped the seats, were funny and entertaining. The Kids enjoyed the theme. My grandson fired the 'cannon' and it was great. Steering the ship was fun for them and the captain was great. The only short coming was, the crew appeared to be well versed in Great Lakes Pirates. I wish they would have had something in writing! I think the crew could compete with SNL! read more

Spent our 32nd Anniversary on the 29th of August, 2019. Sunset sailing on the Tall Windy from the Navy Pier was spiritually amazing. #unforgettable read more

Let me tell you all the fantastic things about this tour: Fun Crew- they obviously have fun and enjoy what they are doing. I was free to roam the ship as I pleased which was nice. They even let you help them out with the sails. #piratestatus The guide was knowledgeable and easy to listen too. The Bar- fits right into the theme. Pirate's punch was VERY tasty and worth spending double in my opinion. The boat was never rockin to hard for a full drink! Snacks were available too. Location- Navy Pier...duh of course its great. some other things: family friendly, great skyline view, really great photo ops. Go check it out! read more

Ahoy! We came here for a school trip. The kids had a blast and the teachers too enjoyed it. The tour guides on the trip took the time to explain everything to the kids very well. I'll definitely try to come again. read more

I lived in Chicago for almost 9 years and I have done countless architecture tours (love!). My friend and her 10 year old son wanted to meet up in Chicago for a weekend and I wanted a really fun surprise for him. I booked the 11:45 pirate cruise. I thought the pirate stories would be a lot more interesting to him than hearing about buildings. Before the tour, we went on the ferris wheel and played a little game of Eye Spy. He knew he had a surprise coming, but he didn't know what. When he saw the ship coming into port, he got so excited! We had a great Autumn day weather-wise and knew enough to wear appropriate layers for the transitions between shade and sun. I liked that you had the options of either enjoying the peace and quiet on the high decks or listening to the entertaining storytelling on the main deck. We did a bit of both. :) We also helped raise the sails, which was really fun. We had a great time and it was the perfect outing with a family. On that note, I didn't care that the bar didn't have a lot of options, since we weren't there to party. As we were getting off of the boat, they said that they are adding concert cruises next summer. That seems like a good adult option to be able to enjoy the boat and the beautiful views without the kids. I saw some other comments about the captain being grouchy and the staff not caring about safety. That could not be further from the experience we had. The captain was not participating in the pirate antics, but that was just fine with me. His job was to focus on running the ship and he was very nice about it. The crew was very informative. They went over safety rules more than once and any time there was going to be anything to watch out for, like a boom crossing, they gave warnings and blocked the pass until it was safe again. I thought they did a really great job. We bought tickets in advance and there was a problem scanning them. We were there 20 minutes prior, as recommended, and it was more than enough time for the girl in the booth to manually enter them and get us into the line to board. I would absolutely do this again! read more

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I booked a 16 person block for my department outing and things couldn't have gone smoother. I used the groupons with drink tickets and redeemed the vouchers on their website. I brought the printed tickets and proof of drink tickets and that seemed to help the cashier a lot. The photographer was even able to get all of us in a souvenir shot! The ship itself is gorgeous and the tour affords amazing views. The bar kept my executive and team well lubricated along the way. The docent in pirate garb was a riot and did a great job at entertaining folks on the lower deck (drinking means you don't remember what you learned about helms and decks and such). If you're in the market for a lake outing I highly recommend Tall Ship Windy for everything from their knowledgable customer service to their beer cooler that fills cups from the bottom. I will likely look them up for another tour soon. read more

Took an "architectural" tour on a Sunday. The ship is lovely. We sat right under the front sail and it was awesome. As others have noted, the ship hardly feels like it's moving, bc it is so slow. At times the ship was even idle. Though I found it relaxing because I was with my love. After sailing a bit east of navy pier, we sailed south to Monroe Harbor and headed back to dock. We bought our tix on Groupon ($50 for 2 tix which included 1 drink ticket). I then reserved our seats online for $2 each and paid tax, bringing the total to $62. At the end of our tour an employee announced that tips in the form of 10's and 20's are appreciated, and 5's are ok as well. I thought he was joking but as I was leaving sure enough Skipper was on shore with a treasure chest (tip jar). WOW. In my years in hospitality I have never suggested a tip from my customers, let alone how much. Pretty appalling considering my end of the ship received ZERO architectural facts from anyone. I feel like my tour more so mimicked what I would expect from the pirates tour (poor jokes and a performance from the crew). In short, I enjoyed myself, but not enough to go back. read more

I had a blast! The weather was beautiful which helps. make sure you check the weather before booking because it is a rain or shine event. The staff was amazing each of them did thier part and stayed in character. The tour guide (I think his name was DAN) Was wonderful. Not only did he stay in character, he really knew his stuff! I learned so much about Chicago from him. And he answered questions patiently and with a good attitude. The crew let you help sail the boat if you wanted that was super cool. My first time on a sail boat and I actually got to help, how awesome. The price of this tour was much cheaper than the other tours and the tour itself was longer. Mine was 75 mins i believe $29 for adults and $12 for children. In my opinion this was a much cooler ride than the others offered. I will be bringing everyone on this tour. read more

This was my 2nd time on Tall Ship Wendy. My 1st time was during the summer of 2015 with my daughter!! I must say I really enjoyed myself once again...very friendly, funny, entertaining but also knowledgeable crew!! Thanks so much for the fun, I'll see you guys next summer read more

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We thoroughly enjoyed the experience! All staff members are very friendly and helpful! Highly recommended!!

Great experience, super friendly staff and the tour guide was funny and very knowledgable. Definitely a must.

Lots of fun. Great crew, very friendly and informative. Restroom, beverages and light snacks available on board!!

I saw the Windy on another tour and realized that I wanted to ride on that ship. So, a few nights later my wife and I went for a ride for fireworks. I must say, that was the most magical moment we've had on a trip in years. The crew were friendly and funny, the captain was witty, kind, and steered the ship with more precision than a samurai with a sword (I figured he would like that analogy). By the end of the trip I felt an attachment to the ship and crew. Though we're only in Chicago for a few more days, I will make it a point to come back for another trip with the Windy and her crew. If you are in Chicago, no matter how busy your schedule, take the time to go on a sail with the Windy and her crew! read more

We liked the tour. It was corny and fun but the boat is beautiful. The staff was funny and fun and they offered all kinds of information about the ship and navy pier history. They take your picture when boarding and you have the option to purchase it late.r They are not pushy about this either. It was very cold on the day we went and they had blankets all over the ship for the people attending. I thought that was a very thoughtful thing to do. It was fun and we enjoyed our time on the water. read more

This a lot of fun. I'm not a fan of all the marketing - taking your photo before you board so it can be sold to you afterward. I'd pay extra for just a regular sail - no theme or pirate actors telling stories but that's a personal preference. All in all it's good fun and I recommend Tall Ship Windy. read more

Had a great time on the Tall Ship Windy. Bartender was amazing. My 9 and 14 year old really enjoyed the entertaining pirate stories. Very well done! A fun and engaging crew made for a wonderful outing. We would definitely sail with them again! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Skip the speedboat tours and go to Tall Ship Windy! I've taken the Aaarghitectural pirate tour and the Spirit Ships and Haunted Harbors special they have in the Fall. Both were a blast! These guys know everything about Chicago architecture, and scary-but-true tales about Lake Michigan. The ship is beautiful, as is the view of Chicago it offers! The prices at the bar on the ship aren't too shabby either! read more

There is no doubt that the crew, especially the main crew man is enthusiastic about this boat and his singing but there are a few problems with this cruise. First, as others have stated, it's not a cruise. You go a few hundred yards from the pier and park and look at the city, which is beautiful. Problem is, you sit there for an hour not moving. I took the Saturday night fireworks cruise. City was lit up, fireworks were good. Second, they don't talk about the city or the ship at all while out there. You get to sit there, cold, listening to their Irish folk songs and plug the CD's they are selling? This would be a great cruise if you actually cruised or they told you anything about what you are looking at. read more

This tour was a lot of fun! I'm a Chicago native and enjoyed learning about the architecture of our lovely skyline along with a multitude of other historic bits and pieces. I enjoyed the whole experience--the crew was very friendly, and the tour guide kept things flowing. There wasn't a dull moment. Bonus: the ship is a working sailboat, and they ask for help raising the sails [which you definitely want to volunteer for and is harder than it looks]. read more

Im a cruising sailor and was on a business trip. This sailing trip was awesome and the Captain was great to talk with as I learned lots of detail about the boat. The views lf the city were incredible. Captain Larry and his crew were professional and very fun! Can't wait for my next trip! Cheers, Gregory read more