We’ve taken the tour three times now. Captain Rodney is great as well as the crews, both times. It’s a calm, relaxing boat ride and the scenery and skyline is beautiful. They call on volunteers to come help raise the sails which was cool for the kiddos, especially. They tell some about the city and mostly Pier history and I love that they have a snack bar below deck for drinks and munchies. The first time it was just us adults. The second time was us and two children and both times were amazing. There happened to be a medical emergency while on board the second trip. My friend, who happened to be an RN was able to assist and they were incredibly helpful and accommodating through the whole situation. The entire crew was extremely attentive to the ailing passenger until we could get docked so paramedics could take over. Due to her efforts, they tried to pay it back as much as possible and were kind enough to give us tickets to bring our girls back for the nighttime ride during the fireworks. That was an amazing experience! We will most DEFINITELY be back again and I’ll be bringing anyone that comes to visit us in Aurora in to the city if for no other reason than to sail on the Tall Ship Windy.

This attraction has the potential to be so much better. The ship ran by motor more than sails. The music was meh. They could totally to a pirate theme or any theme. Instead after 30 minutes you are bored and ready to get off the ship. The crew were very nice. I would love to see them update their sailing tour. If you need ideas let me know. I would also like to do a video interview review Tall Ship.

The whole sailing experience was amazing. The crew was professional, attentive, and engaging. The scenery was beautiful, and it was nice to get away from the hustling city streets. Ticket prices were very reasonable. Would definitely recommend this get away for anyone visiting the city!

Amazing experience. I’ve made it a point to stay away from Navy Pier but this experience was worth the trip. Def. going again soon. Crew is super friendly and the view is not bad either. They actually use the sails to…sail. Recommend 💯🙌🏼

Absolutely wonderful time. Was rained out the first day, but they allowed us to come back the next day and everything was spectacular. I got to hear sea shanties on a pirate ship! Also helped hoist the sails. Very fun.

Amazing trip. Great views of the city. Thought it would be a all motorized trip with sails, but nope, we cast sails and all. Worth every penny, plus they have a bar and snacks. Great boat trip. Highly recommend!

Amazing experience. Must try in Chicago. Nice crew with full entertainment and full bar on board. If you’re lucky you may even get chance to put of the sails.Tip: take the 7pm cruise so that you also get the sunset view.

We chose the afternoon schedule and it was PERFECT. We watched the sunset paired with the calm waters and fair winds, and also had fun talking with the crew. They were always smiling and very talkative yet professional. Music was also playing in the background, totally uplifted the mood. Don’t forget to buy drinks while dancing along! I will try the other tours very soon.

We had SUCH an amazing time aboard Windy! Making views, crew, and company. The fresh sea air and pics were more than worth it ⛵️❤️

Ive lived in Chicago for 5 years or so, and these are the best views (and pictures) Ive had of the city. Thank you to the crew, you guys were super kind and knowledgeable, and I felt welcome on your boat!Overall, the ride is extremely pleasant, theres a bar, and I would 100% book with them again.

What an amazing experience, so much peace and a wonderful view of the City of Chicago, I would it love it too get on the sunset time, but the experience definitely got too repeat, everyone on board was very attentive.

My girlfriend and I had an awesome time on the ship, they let us raise the sails and had drinks, the ship staff was polite and explained how the ships work, will definitely recommend, definitely come with your family.

It was a great experience, and the crew was awesome. Special thanks go to Darwin, super funny guy!

We took our whole crew and had a great time! Kids got to lift the sails and the crew were happy to answer all of their questions big and small!

My friends and I did this as a Chicago Go Pass event and it was great! We called to ensure they were sailing as the weather looked rainy and to confirm availability. It’s very clear go pass users are same-day availability.Got the ticket about 1.5 hours before sailing. Was fantastic! Crew was welcoming, they even invited us to help with the rigging! Ship seemed well kept and clean to us.Music was awesome and added a lot of joy to the environment.Best part? FAMILY OWNED!! Always love to support people who are so passionate about something they will invest heavily into it.Have a good time!

Great time .. would highly recommend it .. and definitely going back sometime .. the staff is amazing and keep you happy and laughing throughout the whole voyage...

I was with friends, and it was an amazing experience! We all had so much fun, I recommend it.

Yesterday was our 2nd time on the ship. Its very interactive, relaxing and fun. The views are phenomenal!

Absolutely loved it. Staff was super awesome and involved. The drinks at the bar was on point. Nice and tipsy by the time we docked. If youre lucky and willing you can participate in helping along the sail out to the ocean. Went on the cruise right when the sun was setting so perfect views. Nice breeze. I was even able to help haul the line. Would definitely recommend.

So much fun! The crew is so friendly and the ride is so relaxing. Such great views of the city. We went on a 7pm cruise and it was one of the best things we did. Even the teens had a good time. They let people help raise the sails. They were also very friendly with everyone.

The one thing I would have wanted to know was that you need to be flexible about when you sail. There are hints on the website, which prompted me to contact the company. They are very responsive but more positive than realistic about departure.If you really want to sit at the front or sit by the captain and possibly steer, I recommend you upgrade to the preferred seating. There is an opportunity to raise the sails. This also could be a reason to seek first placement on the vessel.The cruise features Irish music, pirate themes, and alcohol, something to consider if you have children or your music tastes run strongly in another direction. The historical side of sailing or adventure tails would be more my preference, with a limit of 3, maybe 4 songs so the program is more balanced. I also thought intentional quiet to just enjoy the sounds of the ship in the water would have been nice after we got underway. Just a moment to take it all in.Overall, its a really good experience and the people who own the boat are doing their best to accommodate everyone.

Great view of the city skyline. The crew are professional and entertaining. Great way for novices to experience the joy of sailing. You can even help the crew raise sail!

I absolutely loved the sailing experience!! The crew and captain are wonderful, knowledgeable, friendly people. The boat is old, and every little imperfections give it great character and charm. It was a cold day but it was a relaxing and enjoyable trip. Not sure what the bad reviews are about but we had a wonderful time. Thank you all for your hard work and dedication. ♡

Awesome 😉😃😍, perfect weather for sailing ⛵

My group and I had the BEST time with our experience with Tall Ship while exploring Chicago. Beautiful way to view the city and such a relaxing adventure. Crew is professional and personable. You also cannot beat the price. It was one of the best highlights of our trip.

Worth every penny. Lovely day on the water watching the Blue Angels. Crew kept us informed as to where the jets were coming from. Turns out one of the crew was monitoring Blue Angels radio frequency. The jets were using us as a marker! One of them even buzzed us at relatively low altitude. A great experience!

Had a wonderful sailing experience & would definitely sail again!

We were searching for something fun to do with a friend visiting from out-of-town and joined a recent Windy cruise (skyline tour, 7:00 pm). It was a great choice and we couldnt have been more pleased. There are lots of river and lake cruises to choose from but the Windy is the best in our view. The ship is wonderful and has lots of room to spread out without feeling crowded. The crew are very professional and focused on safety, but also super friendly. The raising of the sails process was especially fun. Windy is a family-owned company and a great choice if you want to chill on a safe and fun ship and enjoy the Chicago skyline.

Absolutely amazing/expert crew and team & Great views with good price !

We took our daughters, sons-in-law and grandchildren for a sail on Windy. We had a wonderful time. It was very warm, so when the wind caught the sails it was very refreshing. The crew were very people friendly. They let the kids help pull the sails up. They loved it! We definitely have to do this again.

Incredibly fun experience! They ask for volunteers to help raise the sails. We went on a fairly calm day so I would describe the experience as educational and relaxing. I would imagine on a windy day it would be pretty exciting!! If you would like to get drinks on board, be sure to purchase drink passes before boarding.. A+++++ HIGHLY RECOMMEND

I went on the tour with my family. The crew was professional and provided an opportunity for guests to learn about ships and help maneuver the vessel. My seven year old nephew assisted with the sails and his twin sister had a ball with the pirate stories. They were also serious about safety, which we appreciated. The only negative is if a person is disabled, and requires a wheelchair, they would not be able to board the ship. Luckily my mom has a cane and not a wheelchair.

I used the Groupon and got the free drink voucher. The crew is very experienced and engaged with the passengers. Very beautiful views of the lake and a smooth ride. Beware you can really feel the waves in the ship store 😅

My wife & I had a great time aboard The Ship Windy September 12th 2021. That was our 1st time on a sail boat. Great sail, good vibes, good music and good host. See you again next year Tall Ship Windy.

This boat is beautiful! The ride was smooth and relaxing. The view of the city was beautiful. The crew was awesome. They will even let you play deckhand and captain.

I had never been to Chicago before and when my friends and I met up there we decided to give this a try. It was THE BEST decision we could have made as a part of our vacation. The ship itself is beautiful, the crew is super friendly, and the views of the Chicago skyline were AMAZING. I would HIGHLY recommend and I plan on going again if I ever find myself in Chicago.

I was looking for something fun to do at Navy Pier, and FOUND IT! We had a great time on our short Skyline Cruise! So worth it! Thank you crew!

I dont understand the bad reviews, all of these bad reviews are just people showing up late or fabricating lies against this business. Tall ship windy is one of my favorite things to do in Chicago. Staff is always upbeat and know exactly what they are doing, I trust them wholeheartedly. The ride itself is amazing. Thank you guys for the great time!

It is such a great experience! I live in Chicago and I love taking my family on this. And when friends visit the city, I always recommend them to go on the Windy City tall ship. We took our friends that flew in and they absolutely loved it and want to come back again and sail.

We were lucky to have missed the rain that was supposed to hit Navy Pier. The entire staff was very friendly. Those customer service was excellent too so we’ll informed and polite.The drink Mermaid 🧜‍♀️ was yummy!Don’t forget to tip!The only thing I disliked was the music selection 😅

Worth the money for VIP tickets to get to board first and get good seats &Carmen was very enjoyable to talk to during the ride! :)

Registration was easy. They are located right on Navy Pier, so there is a lot to do in addition to the cruise. The crew was friendly and educated. The views from the lake at sunset were incredible!

Went on the Tall Ship Windy tour of Lake Michigan on the 4th of July. My group had a great time seeing the sights from atop the ship! Staff were all very friendly and informative and did a good job of making sure everyone on board was safe. The drinks on the boat were pretty good as well. Thank you for a great time! :)

Never been on a sail boat but very pleased I chose the Tall Windy. Crew was very polite & knowledgeable. Found out later that the ship is family owned which makes it even better. Definitely a calming and relaxing experience. To ride at night under the stars plus the fireworks was one of the ultimate romantic nights.

I was meeting my sister for the 1st time in 46 years. She was flying in from Tennessee. I wanted to show her the awesome views Chicago has to offer. I did the other boat tours before but wanted to try something different. Im so happy that I went with the sail boat. Captain Bruce was awesome!! He has a great playlist!! The rest of the crew was very nice! I dont leave reviews. But I made awesome memories on this sail.I HIGHLY RECOMMEND GIVING THIS THIS BOAT RIDE A TRY!! Psst.... the drinks are well worth the cost!! Trust me you can taste the alcohol!! Thanks Windy City Sail!! I cant wait to come down and sail with you again with my friends next time!!

Liked it! Whoever the DJ who was playing songs was awesome! Maybe 20 to 30 minutes of education about Lake Michigan, Navy Pier could be interesting to add to the tour and beneficial for international travelers??? Interaction of pulling lines/ropes was good. Definitely good for first timers to Chicago

The staff and crew went out of their way to accommodate and reschedule us after terrible traffic delayed our arrival and made us miss our sail time. We rescheduled a sail 2 days later which ended up being so much better weather-wise than our initial day. The crew of the Windy was awesome, especially Captain Ralph. They were warm, friendly and professional. A winning combo overall. Highly recommend!

Great quality and value!! Gave everyone a chance to be involved in the sailing experience. Helped each guest feel appreciated and at home. T was our first time and we WILL be back! Cant wait to share with rest of our family!

Sit at the front of the boat toward the dock side for best views. They HEAVILY favor the dock side of the boat for views of the fireworks and skyline. The VIP line went straight to the best spot not sure If they were informed or it was a coincidence. Know that the sails( they are down during fireworks its just the ropes) will obviously impare your view slightly of the fireworks. Bring a sweater or jacket it gets chilly. If you cant sit dockside sit facing that direction. Wednesday fireworks sailing.

My friends and I missed our scheduled boat & they tried their absolute best to get us on the next one. They were very polite & the staff on the boat were very fun and energetic. I enjoyed some of the chats that we had. Would come again!

What a unique and fun experience!!! The crew was knowledgeable, friendly and entertaining! Perfect way to experience the skyline of Chicago! Thank you Tall Ship Windy for wonderful memories!

Wow, what a fun time! We enjoyed a beautiful view of the fireworks with a really fun staff!

My 11yr old grandson had fun raising the sails, and steering from the helm. I enjoyed the scenery and quietly sailing along on the wind. The price was right (compared to other attractions here). This was money well spent and super A+ for kids.

The family thoroughly enjoyed the night-time sail. Beautiful view of the city at night. The boat wasnt as crowded as I expected. Everyone had a place to sit.

We arrived about 40 minutes before departure for the fireworks cruise. The upper decks filled up before we boarded, but we had our choice of seats on the middle of the boat. We had an open air view of the city, which was gorgeous lit up in the night. The ship pulled up right in front of the fireworks, so we had a front row view. The show was only about 10 minutes, but the cruise was definitely worth it even if there hadnt been fireworks.

Accidentally booked for the wrong day. Booking was in place for all of one hour before I realized my mistake, cancelled and booked again.They refused to refund any of my ~$88, but instead of telling me that right up front, gave me the phone run-around, promising to look into it for me. That was last week, and it comes as no surprise to me, I havent been contacted and no refund has been issued. Im sure thats where they plan to leave the matter.Its almost predatory. If you plan to book, youd better double-check. They are not dealing in good faith and are looking to hurt you if they can find a legal way to do it.

Just a beauty!

Our family had an outstanding time on the Tall Ship Windy with Captain Ralph and his crew. We went on the Pirate cruise and our kids, age 13 & 9, loved helping the crew raise the sails and learn about the pirate lifestyle. The weather was incredible also making for a great sail. Definitely worth every cent.

This was a great experience. What I like best was the announcer!!! He did a really good job making us laugh!!! It was fun

We went for a family outing for my mother-in-laws birthday and the whole family loved and enjoyed the experience together ❤

We had so much fun on our sail, the views were incredible and the crew made us feel safe

Paid over 120 dollars and asked for a refund because there was no specific direction and asked every worker there and they had told us that the boat we paid for never existed. We ended up going on a same boat that was cheaper. Called them the next day to get a refund and they’re keeping our money for a boat we didn’t even go on and blamed it on us for not getting on the boat when we called over ten times that day. Reviews on Yelp had a similar problem where they took their money and refused a refund.

My husband and I had a great time! The crew was engaging, knowledgeable and patient. We would go again👍🏻

It was fun raising the sails. The views were great. The ride was very relaxing. The staff were all very nice.

Great experience for both natives and tourists. Bonus points for being the last family owned ship at navy pier and one of if not the last family owned business on navy pier. Will be going back soon! Guests are able to help raise sails which is a cool experience! There is a fully functioning bathroom aboard as well as a bar with both alcoholic and non alcoholic drinks at a price that is very reasonable compared to the rest of navy pier.The person guiding the safety brief/MC was very entertaining (Kaitlyn/Kathen{hard to hear behind the mask}) and the crew was very helpful and friendly as well as the folks at the booth.I wouldnt count on getting tickets the day of! Plan in advance and it is worth it

It was amazing ! I will come back.So calming.

Had a great time going out on Lake Michigan. Very relaxing and enjoyable experience with fantastic views of the city skyline.

Fun group..It was interesting seeing the sales go up.The views of the shoreline were spectacular.

It was a great day for sailing, warm and sunny. The crew was great! I will use this service again in the near future with my children.

The best ship and crew!Most beautiful 45 minutes you will have on a ship. Makw sure you dont use to much Rum, though. 😉

What a fun, interactive, and informational tour. It was great to help set the sails and learn about the ship, as well as the history of Chicagos high rise buildings. What. Fun tour, it is always good to be on the water

What a great ride on the lake, took the evening trip and the skyline looked beautiful

Great evening cruise with excellent crew. We loved every minute!

If zero stars was an option I would totally give it! I came last week to get tickets and they told me that the boat wasn’t operating at all that day. I rebooked for next week. Arriving at the ship they said that they needed some part to be delivered and that the 1 PM boat ride was canceled. This was the second time this is happened. Upon going to the man at the ticket booth, he was very rude. When asking to rebook for a future date this “comedian” says “Well I cannot book for the past.” After rushing to make it in time I was definitely not in the mood for jokes. And of course parking isn’t the easiest downtown so we were already tired.

It was just fantastic!! Very nice experience, 100% recomend.

They are not very attentive to customers needs. A tornado was in effect and they still ran the ship instead of refunding customers. They rather risks life’s than wait for a better day especially people with children.

We had the most pleasant experience sailing with Tall Ship Windy. The crew was very kind, and answered all our questions. I would highly recommend it to everyone!

Purchase through Groupon for Wed 7pm.Called ticket booth to confirm reservation. Was told it was full.They said could go Thur instead. Thur they said the we did not show up Wed & we werent allowed to go.Poor communication between Groupon & company. Talked to 3 different people.one said we could go,2 at dock said No.I cant find how to get refund. I do not recommend Groupon or Tall Windy Ship.BAD BUSINESS.. Zero Stars

Really good experience, friendly staff and great service.

Yes yes yesAmazingOmg how much we loved itWe went for the bout ride and it did not disappoint by any means so yeah we cant wait to come back and have some more fun and walk around here and watch the seagulls hahaha that was fun, they come really close to you sometimes

My friends and I had a reservation for this ride and we arrived 2 minutes late exactly. The ship was still in the dock and they didn’t allow us to aboard. They saw that we ruining all along the pier and they were so rude. We know we were Two minutes late literarily but it was very disappointing to see that they could help us because the ship was still there. So.. we lost the money. Today was 4th of July and everything were crowded, so they couldn’t do anything else and they treated us very rude at that time.After all, I have to say that we stayed there for 2 hours waiting to see if we could do the trip at the next time even though they said they were sold out. And at that time they could help us and we finally did the trip on the boat.The experience was amazing and we had a very good time in the sailing boat. The staff of the boat are so nice and kindly.So, at the end I can say that you should do this trip on the boat if you go to Chicago. It is amazing. You only have to be sure to arrive on time because they leave on time literarily.

We rode the Tall Ship Windy on 7/23/2021 for our 33rd Anniversary and we had a great time!!!

Best tourist attraction of chicago. It old ship that sails. It gives best view of Chicago. Around 1 hour ride. Thought sail I enjoyed the view and winds. You can buy beer on deck. Its from Navy pier. Must visit. The staff is friendly too.

Great experience a must do attraction. Crew was great and very informative to the questions we had.

I was not impressed with this ship. The ride was decent but they never told us to not sit in the front of the boat because they would be moving us every 10 minutes. Unhappy because the kidsnhad to stay standing..

Amazing Experience on a sailboat, Staff was so nice, actually came back and went again a few days later. Such a peaceful trip, with some fun facts thrown in. Take the trip, its worth it !

Pretty good sail boat trip. Not much of a tour, just a loop into Lake Michigan and back to the dock.

Awesome experience! The ship and crew are absolutely amazing! Great fun for the whole family.

A perfect sail by a well trained crew and first rate skipper.

Fireworks cruise was totally worth it!! I suggest you upgrade to VIP especially for the fireworks. We will be back!!

They sell out all the tickets to everyone walks there, they dont consider a place for people who have go passes. Being there 2 hours earlier, they say its all sold out and theres no space, even though we had a pass from a month ago and the pass says you should be there 30 mins early. Rude customer service that refered to our go pass as a discounted underrated ticket.

We have the most amazing sailboat trip ever!

Would like a more diverse crew and music offering.

Amazing experience! Thank you Nick and the rest of the crew! We had such a blast!

Amazing! So good to be back after so long . Happy sailing on the high seas

Perfect!!! Friendly, knowledgeable, funny staff... It was a beautiful sail!!

Excellent boat ride, can’t wait to go again!

Great time and even better crew. Wanted to give a special thanks to Gavin our on board bartender for the trip he made the best ship wrecks drinks and the captain.

It was fun but the captain Bruce was very rude to an older asian couple who was asking him some questions about the ship. He only stopped being rude when he noticed the group I was with staring at him and seeing he was making us and the couple uncomfortable.

Should not be operating, crew does not keep up with proper maintence. We bought tickets for one of their pirate cruises but when the ship came in it had a gearbox failure on final approach and collided with the Odyssey II dinner cruiser. Ended up missing out on the cruise, though after that incident Im glad I didnt end up on that poorly maintained rustbucket they call a tallship. Ended up reporting the incident to the higher-ups at Navy Pier, dont know if they did anything. They badly need to be bought out by someone who actually cares about tallships, the Windy is just crying for help and its cries fall on the deaf ears of her crew.EDIT: The below correction refers to a different incident. This was an incident that happened a few years ago, the ship had already made its way into port but was stuck in gear.