It was pretty chill and relaxing, but also kind of boring!! There was no music playing most of the time, and when it was, it was super slow sleepy music. Also there was no tour and the captain basically just interacted with the children, which was cute! Also the engines messed up and we had to get a tug boat, to get us back the dock! 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

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AWESOME TIME!! Saw the fireworks from the best place!! Fun crew and amazing sail!! Absolutely worth it! This is the boat tour to do if you are In Chicago! I want to go again during the day so bad! Loved it!!! read more

Tall Ship Windy - NJSHORESHOTS girls team & their last night in Chicago on the Windy! Zack gave a great shout out to the girls! Thanks for the pic captain - Boating Near Me - Chicago, Illinois

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

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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

This should be on your bucket list. This ship is a pleasure cruise. If you want to make it even better sail on the Marshall Vente Jazz Cruise. Twice a year you can transport yourself to the tropics for a wonderful night of sailing and music. https://tallshipwindy.com/marshall-vente-jazz-cruise/ read more

Tall Ship Windy - https://tallshipwindy.com/marshall-vente-jazz-cruise/ - Boating Near Me - Chicago, Illinois

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So much fun!!!!! We had a phenomenal time on the sunset cruise, the music and the scenery was great and the crew is so friendly. Highly recommend! read more

Wonderful experience! A 75 minute boat ride with a wonderful crew. Took tons of great photos of water, light house, sky line and sunset. I was given an opportunity to help raise the sail, (hard work), and lots of great conversation with the crew. Our favorite crew member, Carol, answered all our questions and indulged is at every turn. The boat had a well stocked bar and snack cantina. I highly recommend taking the tour, we had a blast! read more

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Ticket rules say arrive 30 minutes early! You must check in at the ticket booth. My autistic son loves pirates and dinosaurs. No dinosaurs were on the ship except the ones we brought with us. But none are needed. The crew was wonderful. They explain the rules well and enforce them politely (not very pirate like but effective nonetheless). The pirate stories were entertaining, especially the first one. Interactive for the kids. Jokes for all ages. I can't remember the pirates name ( spice and everything nice I think). They passed out blankets. But bring a jacket! The ride was smooth. Beautiful skies on the 715pm ride. They have a collection of things in the bar area for sale. We bought backpacks. My sister had a female bartender and her drink wasn't strong. We will be back again when we are in the area! read more

Tall Ship Windy - A pirate that smiles! - Boating Near Me - Chicago, Illinois

I loved riding with the wind, I got great photos, and the crew was great! I decided to purchase the photo because this is most likely a once in a lifetime event with my sister and the photo behind the ships wheel was perfect. We were comfortable sitting on the wooden boxes and could see everything. read more

Would not recommend. Snack and bathroom area had a stench like no other. Operator's not overly friendly and made sure we knew tips were accepted/ expected read more

Great crew and some fun facts learned on Lake Michigan pirates. Weather was chilly, but they have coffee and hot chocolate and blankets if needed. Excellent sailing and the view is amazing. Crew is great and super knowledgeable...fun times! Tickets are easy to purchase and ship is easy to find. Worth it! read more

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

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I took a group of students on Tall Ship Windy yesterday. It exceeded every high expectation I had! Every single staff was knowledgeable, patient, and very helpful. I will most definitely be back. Even the prices at the bar were reasonable. Wonderful experience and worth every penny. Was also pleasantly surprised with the inclusivity of the ship and staff :) 10/10 would recommend and return! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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What a pleasant surprise. Anything with a "pirate" theme could be really cheesy or bad. This was neither. Instead, you get a nice tall ship with a really friendly (and young) crew who seem to just be enjoying having a fun job for the summer. One of them told pirate stories on our ship, while others showed the kids and adults how to raise the sails and steer. And it's a bargain compared with the other cruises out there- $25 for a full 75 minutes. Definitely recommend for families and for couples that want to walk around a big sailboat. read more

My friends and I bought several LivingSocial deals to go on the weeknight Fireworks cruise on the Tall Ship Windy. It was OK, but I was a bit underwhelmed. Mainly, by the bar. As suggested on LivingSocial we purchased the upcharge for $10 in bar credit, and were looking forward to some boozy boating fun. The 'bar' had: * Budweiser * Wine (from a bag) * Rum * Cranberry Juice That's it. I would expect at LEAST something decent to mix the rum with, if that's all you've got cocktail-wise. Two of us ended up spending our credits on some candy & snacks, and the others didn't bother spending it at all. A waste. The ship ride itself was fine, a bit boring since we pretty much just motored out onto the lake, then raised the sails for 5-10 minutes before stopping and lowering them for the fireworks, then headed back in. All in all, I'm glad I had a LivingSocial deal, because full price would have felt like a ripoff. read more

I came here with my gf Saturday 4pm. The hosts on the ship were funny and had some good pirate stories. However, it was too cold, despite the blankets they gave us, and we ended up ducking inside the ship to stay warm. 75 min cruise, need to arrive 15 min early for safety orientation. read more

I am livid about the way I was treated. 1. We sailed at 1 pm on a Monday. 2. I am disabled. I wear leg braces, use a walker/cane, and my fingers are 95% paralyzed. 3. The crew would not let me bring my walker aboard because it had wheels (my cane also has wheels). It has two wheels and two skids. 4. I got onboard and I struggled to find a seat on the lower deck. 5. At the conclusion of the trip, I struggled to walk across the deck without my walker. 6. Some crew members asked if I needed help. Hmmm....take away a tool that helps a man to walk and then ask if he needs help. This is degrading to me and stupid or cruel on their part. 7. One crewman offered to have my walker available at the bottom of the stairs on the deck side. Obviously, problem solving is not strong with this one. Why are they intentionally making it more difficult for the handicap? read more

Ahoy! Captain John and the crew gave us a perfect afternoon architecture cruise. Austin was authentic in his love for the city and very informative about the Chicago skyline. Just the right amount of talk time and peaceful sailing time. The ship was spectacular with four masts and a grand salon with cold beer. We had about 50 on board and all were smiling. Perfect length of tour and great options to eat nearby too. Groupon makes this an awesome value. read more

Tall Ship Windy - Chicago skyline from Lake Michigan - Boating Near Me - Chicago, Illinois

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An afternoon on the Tall Ship at Navy Pier was great. Being on the lake under sail power is beautiful as are the views of the city. Myself, 2 daughters, and 2 grandsons enjoyed the ride. My grandson helped hoist the sail and stood at the captains wheel for a thrilling experience. KOD read more

Unenthusiastic crew- no commentary-- just a few pirate cliches when boarding and exiting and the "ask" for tips. Socially distancing not enforced at all-- it's up to you to tell people not to sit so close, but becomes impossible because there is no limit to the guest boarding. The thing that bothered me most is the lack of pointing out buildings talking about the skyline, Chicago, etc. we went out straight East and then back-- didn't even do the shoreline-- pick a different cruise - read more

We had the best time. Weather was perfect for sailing. The staff and crew were great .Used Groupon for tickets which is a good saving. Just beware you will need to pay service charges and taxes even with the Groupon. read more

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We took the 3:00 cruise today. Weather was absolutely perfect and so was the crew! The crew on the aft deck was so knowledgeable about Chicago and had a vibrant personality. I'm sorry I didn't take the opportunity to interact with them one on one. Wonderful experience. I would highly recommend this outing for an alternative view of our beautiful city. read more

This was quite an experience, the staff were very friendly and weird enough that you feel that you are on a crazy pirate boat! The first thing that you'll learn on the boat listening to the sailors tales is that they are all family and the boat is their family business. The experience of raising the sails and working on the deck, the silence in the middle of the lake and the beverages on the bar are special experiences that you must have. I would definitely try their 7 hour trip next time in Chicago! read more

Was advertised on instagram as a sailboat and wine experience but ended up being a pirate ship. Honestly pretty funny that that happened but I would've liked to have known what i was getting into ahead of time. Made me want to walk the plank. read more

Past experience was fantastic with the crew and very entertaining. Recent experience dropped the rating. Just had a terrible experience with trying to book another trip with the customer service rep who was not friendly and rude. Ended up booking elsewhere. Make it easy to buy. May try later in the summer. read more

This was surprisingly good. We went for the Pirate Stories your. The lead pirate, Shark, had very engaging and entertaining stories. The content was child appropriate with adult jokes sprinkled in (think Shrek). We'll definitely be back in the future! read more

I took my friend on the lighthouse tour when she came to visit and really wish I hadn't. The ship was moving suuuper slow, so all you got to see on the "tour" was a lot of water and we got nauseaus from the rocking. A lot of people were sitting looking like they're about to vomit. Price isn't that great either. With LivingSocial coupons it was supposed to be $15 per person, but when i went to get tickets online, they charged me an extra $15. read more

Great, relaxing experience. Views of the city skyline are fantastic. Really enjoyed sailing on a tall ship. read more

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I booked this tour a few hours in advance. I'm from Texas and this is my first visit to Chicago. No clue about anything. Got stuck downtown and couldn't make it in time. Literally 6 minutes late. Boat was gone. The young don't girl at the box office was of NO help. Her exact words......."There's nothing I can do for you" My review is on the service or lack there of. If this is how they treat paying customers, I don't care to be on the boat really. I could see the boat sail away. I'm guessing the insurance would have allowed me to get help at the box office but I was willing to pay for another ticket. I'm not satisfied with this company customers service and I would like to be contacted by a supervisor or manager to further discuss. read more

So this started out well. I purchased two gift certificates in December as a Christmas present for the sweetheart, ya know, Christmas in July. No problems there, two adult fireworks cruise certificates plus taxes and fees, my money eagerly gobbled up. The problems started when I went to make the actual reservation online. The site was trying to charge me taxes and fees again which I had previously paid. I sent an email and by two days later had not received a response. So I called. I got a woman on the line who was pretty short with me, said I still owed money for taxes and fees. I already paid them, I said. She claimed it's taxes and fees on the reservation. Why would there be taxes and fees on a gift certificate and then more on setting a reservation? It doesn't say that on their website nor on my receipt nor, well, anywhere. So, no. She got impatiently testy with me so I had to explain that I wasn't trying to be difficult. I had paid for the cruise in full in December, why would it be different when I go to use the certificates? Do you charge taxes and fees twice when someone books online when you're open? No? You shouldn't now either. She hesitantly forwarded me to her manager who I was told would say the same thing, that she was in but I was only able to leave a voice mail. "She'll call you this afternoon," I was told. Nope. Their "contact us" web page doesn't appear to be working. I ended up contacting the site that manages their online pay system looking for my full receipt. Thankfully he ended up resolving the whole issue for me. It was a glitch that everyone knew about but did nothing about, so beware. I wonder how many times they collected taxes and fees twice. Ahem. In the end, the cruise was nice. The pirate-y stuff was eh, pretty campy. You best be sure to turn your flash off on any camera -- the group was yelled at several times. They take your photo before (and get testy when you refuse to as they want to sell it to you at the end), drinks were expensive, and they have a big treasure chest out for tips exactly as you get off the boat. It was nice to be out on the lake, be on a big sailboat though for the most part the sails were down, see the fireworks from that vantage point but I don't think we'd do it again. read more

A nice relaxing trip. This is a fun activity for any age. We did the pirate cruise but they offer other themed trips. You set sail from the docks at Navy Pier. You can get some beautiful pictures of the coastline while enjoying a tasty beverage on the water. Buy a drink/snack card at the ticket booth. You'll save a few dollars. You can help hoist the sails, listen to true pirate tales and if you ask nicely the captain will let you take the ships wheel for a quick pic. I suggest getting a seat on the foredeck (front) if possible and if you want a drink get it as soon as you get on otherwise you'll wait in line for a bit. It would have been nice if the pirate stories were told over the speakers instead of just on the main deck. Overall a great way to spend some time on the water away from the busy city. read more

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Enjoyed the whole trip what I didn't like is when they put politics in the trip, didn't appreciate the remarks made about President Donald Trump. He was the best ever and that was not the place to reflex your opinions. read more

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

Great experience on the boat..cant believe iv never gotten on this before...30 bucks a person for 75 min on the lake I suggest going on the 9 o'clock trip better pics guaranteed . It's a hands on experience all the way...bar downstairs. Will definitely be back read more

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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

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

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

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

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