One of the best things I did while visiting Chicago! I booked the 8:30 p.m. Tall Ship Windy sail, and it was worth every penny. We left around 8:30 to 8:45, and by the time the 9:00 p.m. fireworks started, we had a front row view from the water. It was absolutely incredible. The captain and crew were friendly, welcoming, and did an amazing job. The ship wasn't overcrowded, so there was plenty of room to walk around and take in the views. Watching the fireworks with the Chicago skyline in the background was unforgettable. After the fireworks, we sailed under the night sky with the sails up and great music playing. It honestly felt like I was in the Caribbean, except with an amazing city skyline all around us. I'm from New York and was in Chicago for work, and I have to say this was even more impressive than seeing the New York skyline from the water. I also own a sailboat, so I really appreciated how well the crew handled the ship. One of my favorite parts was that guests could even help hoist the sails. There was a full bar with a really good rum punch, and so many great spots to take pictures of the sunset and the skyline. The crew was also happy to take photos for people. If you're going, get to Navy Pier early and enjoy the restaurants and drinks before your sail. This is great for families, couples, or even if you're traveling by yourself like I was. It's a unique experience that you won't get on one of the regular tour boats. I would absolutely do this again the next time I'm in Chicago. read more

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Staff was so amazing and kind, relaxing way to see the city on a calm and quiet sailboat so much fun read more

Tall Ship Windy - Hoisting the sails - Boating Near Me - Chicago, Illinois

Observed the air and water show during a family visit on the tall ship windy! We encountered some unfavorable weather which forced us/the ship to change plans with sailing times. There was some confusion about how we would go about rebooking and when, but we got it sorted eventually (basically, you should get the travel insurance). This 5 star rating is specifically to the guest services folks (one was named Tate and his coworker - not sure of her name) and the very energetic and informative gentlemen that led our tour on the boat. It's the hardworking crew and service workers that make this a good experience. Thank you Tate et al! read more

We went on the ship for our 5 year anniversary to listen to Michael Charles and his group, and we were amazed!!! The ship is gorgeous and there is so much space on it to sit and relax or to get different views, the actual view of the city you get is incredible. The whole crew, captain, and owner were great people who made us feel like we had been coming for a while, and we made some new friends on the ship too!! 10/10 would go again! read more

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Wonderful experience on an awesome ship. Definitely a worthwhile and unique experience with the fireworks cruise, I look forward to a day time sailing in the future. The crew were very friendly and knowledgeable. Outstanding all around. read more

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The Tall Ship Windy is a fun way to see the harbor from a vantage point that most of us never get! It was a fun way to spend some time with friends and family while being out on the lake, the only sound being the wind in your sails. And the occasional pop of a top from the on-board bar with snacks and drinks. And sometimes a sea shanty. And the tales of Lake Michigan piracy from Andy the Kidd, our fine narrator for the voyage! And the firing of a canon at the lighthouse. But other than that, very peaceful! read more

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It wasn't exactly sailing, more like floating. We sailed out about 1/3 of a mile and just bobbed in the water. They had a story time and some other theatrics like raising the sails but that's not why I booked this excursion. The crew were absolutely wonderful but the bobbing part wasn't. ( made 2 out of the 3 of us nauseous). Very disappointed! read more

Came here for a mid 30s bachelor party and it was great all around. Even my friend who didn't normally like boats was okay on this. I was tired and able to chill in the shade quietly which I definitely don't think you can do on most tours. Cheap drinks Chill vibes Interactive Learn something What's not to love? read more

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

Absolutely, 100% recommend this excursion. We have gone on countless lake excursions in the past. This one is hands down, the BEST!! Other boats have been ok, but you feel like you are on a Carnival cruise. Massive boats with very little crew interaction. Tall Ship Windy, I found out, is owned by a family, not a corporation, and you definitely get a family experience. On this sail boat you get to actually sail on Lake Michigan, not have engines roaring in the background, and have a peaceful sail while viewing the amazing Chicago skyline. And, what's even more amazing, the crew allows the guests to help raise the sails. No matter what your strength level is, they encourage everyone to participate. They also have a great bar with extremely fair prices for drinks. If you come to Chicago and do not go on this excursion, you are really missing out.. A must do!! read more

Great experience! Andy the Kid was knowledgeable and entertaining. Damian amd a Christian were friendly amd funny. Engaging, interactive and fun. Highly recommend. ​will.certainly book again next time we are in the area. read more

Tall Ship Windy - My son assisting with hoisting the sail - Boating Near Me - Chicago, Illinois

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We had an amazing time. The crew was attentive and helpful. Bring money for drinks and snacks at the bar. The view of the air show was better than I expected. My kids and mother truly enjoyed themselves. read more

Tall Ship Windy - On the ship - Boating Near Me - Chicago, Illinois

Was a great time on the ship. Got to raise the sails and learned lots about Chicago with the nice breeze of Lake Michigan. Highly recommend if you're at navy pier or around Chicago!! read more

A very enjoyable experience! Wife and I went out for a relaxing afternoon and got great views of Chicago. If we ever get back, we'll do it again! The crew members were a lot of fun and the prices at the bar were reasonable, being even to or slightly higher than what you'd expect to pay in the restaurants and bars around town. read more

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

This was a fabulous cruise. It was the 5 pm cruise. I think everyone there just wanted to chill. It was kids light. But just a really relaxing evening cruise. read more

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It was pretty fun. I'd definitely recommend it, even if you also do the river architecture tour, it's a fairly different experience. I'd say it's more about cruising and less about learning. The guy on the microphone eventually just started joking because while he had interesting facts, most people weren't really listening. The ship itself is impressive. It's laid out in a weird way but I enjoyed learning about it from the captain. There was a bar with snacks onboard and we all had a beer and watched the skyline go by. A great experience for locals or for people who are visiting. We went with my folks, in town from Texas. read more

Tall Ship Windy is a beautiful sail boat! Located at Navy Pier, it's a must have for anyone who loves sailing. I purchased the ticket online, and made reservation at the same time, online. It was pretty easy process. With the confirmation, I received the check-in instructions and directions to find the exact location. Check in was 15 minutes before sailing. On the boat, there was a bar with both alcoholic and nonalcoholic beverages, and some snacks for purchase. The crew members were entertaining and fun to watch the work done. They instructed everyone for safety and constantly kept us under control to keep us safe. The view of the city's skyline is amazing from the distance! I had a great time! read more

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I had a great time at the tall ship windy at the navy pier ! Zac made us laugh and the views were spectacular. Worth every penny read more

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

We are local Chicagoans and we live a block from Navy Pier. Friends asked why would we do such a touristy thing? Well, everything about it was wonderful. Terrific staff. Super value. A truly outstanding way to experience our city and our lake! read more

did the fireworks cruise on Saturday, was great atmosphere, great spot for watching the fireworks. Matt from Tall Ship Windy stellar host, quite the character to keep you enticed and laughing. Mark from the Queen Blue not so good was visiting Chicago for first time so only thing would have liked is more fun facts stuff since it went quiet for some time but is possible is just wrong cruise for skyline info/stories. read more

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Our second time on the Windy and it was a vey good cruise on a beautiful summer day. A big shout out to Carol-a worker on the boat-who help retrieve my pricey sunglasses that slipped off my head and fell behind the bench we were sitting on. It was not an easy get (she had to pick them up with her feet!!!) and I really appreciate her for helping me reclaim them. The only negative is I felt too much animated scripted announcements at the beginning and ending. It was too much when we just wanted to enjoy the peace of the sailboat. read more

What a wonderful time! The crew is fun, personable and knowledgeable. We took a Skyline sail aboard Windy the 148ft Tall Ship. Interactive, informative and memorable. My only regret is not taking a longer tour. The sailing is Interactive, the guest get to raise the sails and the Captain will allow you to steer windy. They offer Pirate Story tour, Architecture Skyline tour, fireworks tour and have soecial event tours. I can't give enough praise to the crew! Thank you! read more

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Very relaxing sunset cruise. A lot of tour boats give history lessons the entire ride, which is fine, but this was just a nice relaxing sail with pleasant music and beautiful views of the skyline. My husband is very into maritime history and ship engineering, being on a four mast sailboat with the most relaxing ride was such a treat. read more

My husband and I were both sick, and we couldn't go. I emailed asking for consider of a refund, and we got neither a refund nor a reply. Rude to ignore the email, and disappointed that we couldn't go or reschedule. read more

All of us had such a great time on the Talk Ship Windy!! We did the 7:00 trip. Originally, we had reserved a 3;00 trip but had to change the time when other family members decided to join us, We were so happy that we were on the trip at sunset!! The crew was fun to interact with , the view of the city at sunset was beautiful, and it was fun getting to ride on a sailboat. We will definitely do it again in the future! read more

Such a fantastic way to view the fireworks! Sailed a bit down the shore, too. Beautiful nighttime photos of Chicago's skyline. The crew was friendly and the drinks were tasty. Highly recommend The Tall Ship Windy! read more

Snore fest... Everyone on board was tired and told us so many times on the microphone. Lacked any type of pirate flare. No real sailing, the sails just flapped in the wind and 90 percent of the time no one held the helm and the wheel was spinning aimlessly back and forth with no one steering. $18 for a short run and coke. Some rude staff. We asked for the best place that they thought we should sit on the ship and the crew member answered "Just take a seat" and snarled. (Person with open shirt, scruffy blonde hair and unshowered look) The ship sat in front of the skyline for 45 m with people taking selfies everywhere. Incredible waste of money and time. read more

This was such a fun experience and cute date night activity. I got my tickets online for $22 per person. There's a VIP option but that allows you to just board early and doesn't really add any other value. Seating is first come first serve so do try to arrive earlier to pick your seats. We arrived 45 mins early as it stated in the reservation, but 30 mins is probably sufficient enough. We went during sunset and it was so beautiful. It is a sailboat that fits around 120-150 people and can be a bit rocky (obviously ...it's on the water) so be mindful with your balance! Crew is great and friendly. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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The Tall Ship Windy is an absolute must! As a local in the area, I had a wonderful experience on the boat and highly recommend the 7pm departure. The team did an excellent job balancing safety, engagement, humor, and a joyful piratical experience. read more

To follow up on the review I posted , Bruce from Windy contacted me , he resent the gift card voucher. Looking forward to hopefully better weather next time. My bad. read more

We had a fabulous time watching the fireworks on The Windy. We were very close to the barge that launched the fireworks. The crew were all lovely and friendly. We had a nice chat with the lead crew person. One crew member was helping a family who had a small child not feel well while sailing. They sat with them and distracted the child and tried involve the child in conversation to help distract them. It was very nice of them to reassure the child. The captain had to deal with some crazy boat antics during the fireworks show. He was keeping his eyes on our safety and managed to avoid a mishap of some unaware boaters. It was a lovely way to spend a perfect summer evening on the lake! read more

I have joined the crew twice now for a sail, and for me, this one of the best experiences Chicago has to offer. Modern vessels are fun and fast, but being aboard the Tall Windy really takes you back in time. Just imagine our ancestors sailing across the Atlantic on one of these ships! The crew is friendly and knowledgeable (they even let guests help hoist the sails!), the views of the skyline are exceptional, multiple launch times make it convenient to work in with your other vacation plans and the duration of the trip is just right! read more

A great way to see the skyline at sunset! Myself and 3 other girls boarded the Tall Ship Windy on a Saturday at 7PM. The sunset is beyond gorgeous at that time, and the boat has a nice sail, not overly rocky. If you like to drink they have a nice bar on the inside even set up with a few large tables just incase someone want's to sit on the inside, out of the wind. There's also a small gift shop area. The team is super interactive, Peter and Maddie were excellent. For direction, It's very easy to find on Navy Pier, right past the Shakespear theater & across from Billy Goat Tavern. 10/10 recommend and will be going again. Do the VIP Tickets so you can pick your seat first as you get early access to the boat! read more

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I have sailed on the Tall Ship Windy in 2023 & 2024 and back then some of the staff dresses in pirate outfits and talked about the Chicago Skyline. I was looking forward to learning more about the many buildings in Chicago on my recent sailing. I was disappointed that there was no skyline speech. Also just before we docked, they mentioned that if you were not happy, take out a $100 and write all your complaints and deposit it in the tip chest, they hold and you pass by as you exit. That is the cost of the sailing for 2 people, a 100% tip for nothing? What greed. I used to tip when I heard the educational talks, but not for less service. Captain Ralph is the only good thing going now, if he leaves then Tall Ship Windy will not survive. Captain Rodney walked away from the helm the last time I sailed with him. read more

Wow... what an amazing experience! We had stumbled across Tall Ship Windy after searching for a boat ride with a bar, and I couldn't be happier that we chose this attraction. There was something very calming about sailing on Lake Michigan. We sat in the front with a few drinks nearby a pair of the exceptionally friendly crew, and the atmosphere was perfect. I will certainly be back to experience Tall Ship Windy with more people! read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

Amazing experience. The captain got us so close to the fireworks, the crew was amazing. 100% recommend.

Best part of the trip was seeing the skyline from the lake. Second best part - landing back in the harbor. Here's a tip for the crew - Go to Disney and learn how to narrate a tour! The Architectural Tour had almost no information on a handful of buildings. Boat was too far from shore to appreciate any architectural details, and just sailed slowly, maybe less than a mile, in a big circle. The guide liked to talk. About himself, and other quite irrelevant comments, some a little offensive or politically incorrect. Script sounded as if it were written by middle school kids. Corny and BORING. If you want to learn about Chicago's rich history and significant buildings, a river tour is the way to go. sent from iSteph read more

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

Very entertaining trip out into Lake Michigan in open ship. Also you can pull up the sails to power the boat if you like to. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

Went on the Tall Ship Blues Cruise last night. The band was great! The sailing was not. We basically went 1/4-1/2 mile out from Navy Pier and sat. Not what I expected. Calling this a sailing cruise is not accurate read more

The trip on Tall Ship Windy was awesome! It is exactly as advertised. The crew was great and super friendly. Would recommend t For persons of all ages. read more

The sail was fun and the view of the city at night is breathtaking! We did a Friday night pirate pub sail and it was a fun event. There was a dj with some cool music and the drinks were pretty strong. We expected a little more pirate type events but other than that it was a fun time. read more

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