My husband and I enjoyed the 1 hr sail. It seemed too short though and thought another 30 min. to an hr. would have been great. Some low clouds rolled in that made the shoreline disappear (see pics). The wind picked up which made us move through the water more quickly. Sailboats are fun when the wind cooperates and it did that day! read more

We enjoyed this experience so much and would definitely recommend! The crew was amazing and interactive the whole trip! The directions of how to get to the boat were really clear in all the emails and they even sent an email update when the Navy Pier parking lot was full. This is the only family owned boat left on Navy Pier so you should definitely support them. It is worth it!! read more

Awesome trip. The weather was windy but perfect. This is a must for a trip to Chicago. 30.00 for 1.5 hour trip. Informational and great staff. read more

For the same price of the crowded architecture tours, you can go sailing in a true sail boat and learn history from great storytellers. The drinks are great too! This was my favorite thing we did in Chicago. read more

Was able to order 10 tickets without any issues. Aug 31st, was the last firework show of Navy Piers season. Was very excited they still had availability. Being a full working wooden ship we could feel the "chopy waters". We where invited to help raise the sails! Since they are interactive and a teaching vessel. Beautiful views, fun & funny crew. Very willing to work with us for pictures and making our experience fantastic! They are very reasonable priced tickets! Worth every penny! read more

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I'm glad we paid a little more to have a unique experience! it was a lot of fun, just wished it was 2 hours instead of 75 minutes! would definitely recommend! read more

If you have never been sailing before, this is a great first. We did the sky line sail at 7:00 pm, the sun setting in the background of the city was beautiful. The crew was hilarious. The only thing that could make this ship better is if they added Wouldn't It Be Nice by The Beach Boys to their playlist to make it like the Adam Sandler's 50 First Dates scene. Another perk is the ship has a bar. Oh, and a guy wearing a speedo, riding a yacht, mooned everyone. It was great. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Tall Ship Windy canceled our tour at the last minute for repairs, causing a last-minute scramble to make alternate plans for a child's birthday. After being told that we'd get a full refund, they think it's totally okay to not actually give the full refund promised, but to keep "processing fees" for a trip we never got to take. Calling and speaking to multiple people got me all kinds of variations of "There's nothing we can do about it". Bad form, guys... you canceled the trip, you should shoulder the financial responsibility. I'm out even MORE now, trying to piece together a party at literally midnight the morning before. read more

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

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

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

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

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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Be aware of horrendous customer service!!!! STAY AWAY If I could give this place a 0-star rating, I certainly would! I purchased the tickets via Tripadvisor on August 25th for August 28th. When we came to the booth to collect our tickets we were told that the tickets were purchased for August 24th and we would need to purchase the new tickets to get onboard. While the service rep. kept saying, "hold on one minute" the ship sailed off. It was our friend's Birthday celebration and it was extremely disappointing and upsetting to see our friends sail away while hearing continuous "Hold on a second". The service rep. was utterly unwilling to work with us stating that the tickets were purchased via Tripadvisor and he was not authorized to let us board the ship or issue a refund. When I reached out to customer service for this so-called company they stated, and I quote " Our booking system has nothing to do with your reservation; looks like you booked the wrong date with Tripadvisor." If they are unwilling to work with people who book the tours via. 3rd party, why even offer this service and advertise on TripAdvisor? This company clearly knows absolutely nothing about customer service. All they care about getting your money. I would strongly advise that you stay away, there are plenty of other options out there. read more

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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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

We enjoyed ourselves and the employees were extremely kind. The only thing that I didn't like was the end when they asked for tips and waited at the exit of the boat with a box. It was very uncomfortable for us. Please just raise the price of the ticket and not ask for tips...made many of your guest uncomfortable. 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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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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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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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

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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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

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

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

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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