Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later. read more

Came aboard the Tall Ship Windy with a bachelorette party and had a blast! The crew was super fun and enthusiastic and we got some great views of the city along with some fun facts. Best part however, there's a BAR on the BOAT! Highly recommend this fun/educational event read more

The tour was really great. They took our picture before we boarded, taught us sailing terminology, gave plenty of time for photo ops, and the crew were so kind. Only thing I didn't care for was trying to charge us 25 dollars for 3 pictures of us before we boarded. We only needed one and they said it's all 3 for 25 or nothing. They were nothing really special but for the price of the ticket I feel they should include the pictures as they already had them printed out and everything before you get back. Seems like you'd save more money printing them by request, then wouldn't have to charge patrons so much. read more

I took the Architectural Tour with friends on a trip to Chicago in July. Wonderful experience if you love being on the Great Lakes (I do), tall ships, and architecture. They ask for volunteers to help raise the sails and I did. Quite the workout! Thankfully you have help from others. The weather was perfect and I would definitely recommend it to anyone as a fun and educational city experience. (We took the water taxi to Navy Pier from near Union Station so water travel was kind of the theme of the day. That was fun too.) read more

It was a great experience for our family. The crew were so nice and knowledgeable. My kids loved being on a pirate like ship. The viewing was amazing. I would definitely return back and board on this ship again. read more

we had a very enjoyable cruise with trustworthy and energetic crew. learned a lot about tying knots and pirate history. Only complaint would be that we thought we'd learn a little more about lake history and ecology based o. the promotional material: "This unique, hands-on learning experience is a great way to enjoy physics, ecology, history, and storytelling while taking an active part in sailing the vessel. " overall, a good-enough value and experience read more

The views of downtown Chicago & its skyline were beautiful! The sailboat was quiet and very smooth! The crew was fun, especially Matt, he was very good at telling us about Chicago! 08/13/20237 read more

The sunset time and the ship in general were fabulous and we had an amazing time. However, one note - I stood on line one hour before departure so my family and I could get a good spot to sit. We were the 3rd people to board and we got the seats with the view we wanted.. But then a group of 15 people boarded at the very end and came and stood right in front of us. They were drinking alcohol and being loud the whole time. I felt this was very unfair as it ruined the experience for me and my family. I wish the crew would be a little mindful of this and ask people to SIT somewhere instead of standing and blocking everyone else. read more

What a fabulous time! I will most Definitely be going again. Both kid and adult friendly.

Spectacular experience! Wonderful & fun crew, super time sailing, gorgeous sites of the lake & city and great history of Chicago!

Had a great time! Relaxing ride while seeing the sites of Chicago. Highly recommend.

I had a great experience riding onboard Windy. The crew provided a fun and interactive experience. I was given the opportunity to join in on hoisting the sails and there were many great photo opportunities. The crew is friendly and more than willing to help take photos. Definitely worth a better experience than a regular city cruise which has you just sitting down and listening. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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Gone for a mini family vacation and needed something to do at night that would allow us to see the city lights. Tall Ship Windy was perfect! It's an actual sail boat and they allow you to hoist the sails with the crew! Not a very wordy tour they told you a little about the boat and the parts of the boat and allowed you to enjoy the view. Got a coupon of Groupon and it was very affordable! Would recommend. read more

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

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They treated us like friends. I brought my husband, my friend and her son. They made sure her son got to experience everything hands on and made him feel special. His mother couldn't thank us enough for bringing them and the ride was so relaxing and informative! read more

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

I have been on quite a few sailing ship tours and this was one of the best. Our crew were professional, friendly and worked well together. Nick was the storyteller and his repertoire was delightful. It helped that we had the perfect sunny day for smooth sailing. I will always choose a sailboat over a motorized vehicle and this was delightful read more

I feel scammed by this company. They charged an additional $9.20 for the tickets (2). The tickets used to be valid until September. These expired just a few weeks into the summer which was June 15th. They did not mention that the ship is a minimal replica of a real Tall Ship. It is nothing like the Tall Ships that originally came to the Pier. They mostly stayed close to the pier and didn't go out to the main part of the lake until the end of the trip. Very disappointing. The only positive was a very nice crew. read more

DO NOT, DO NOT, DO NOT PURCHASE FROM HERE!!! Purchased tickets here during the day for fireworks cruise, the weather took a drastic turn it was obvious you couldn't view any fireworks. They would not let us have our money back even though their next fireworks cruise was Saturday well after we fly out of town. STAY AWAY! Especially from the nasty wide woman. read more

Great times! Some of the best views of chicago. Do it twice a day and a night tour. I get this every year from groupon. read more

Tall Ship Windy - Beautiful day out on lake Michigan! - Boating Near Me - Chicago, Illinois

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We had a tremendously enjoyable late night fireworks cruise with our family. Purchasing drink tix ahead was helpful. VIP seating was beneficial. A fantastic view of the shoreline and fireworks. We will definitely do it again!! read more

Found on Groupon while searching for things to do in Chicago. There was a decent discount. It's was enjoyable tho maybe the wind didn't cooperate completely. The crew was nice and Katie was funny. read more

All in all this was a good experience. At $40 per person it seems a little pricey, but we are always happy to support a local, family owned business. Highlights include an accommodating and entertaining staff; a full bar with great NA options for kids and the sober-curious; great views from Lake Michigan. Lowlights include an overcrowded boat, uncomfortable seating (damaged benches and various wooden boxes were used for seating); and the stench of raw sewage that I presume was from the boat bathroom and not Lake Michigan. read more

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

Overall fun experience, great views of Lake Michigan and the city of Chicago. I didn't like the fact their were no actual seats and you just sit anywhere. With covid just ending I was nervous with the full capacity boat. People were too close for comfort for me. read more

Wonderful serene trip on the lake, we enjoyed every moment as well the beautiful skyline and the ability to see three states... Great way to see the sunset over the Chicago Skyline read more

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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

Wow, it's been two years since I last reviewed Tall Ship Windy. I think it's about time to give Tall Ship Windy a shout out and update my review. Firstly, I completely stand by my original review. On my last visit to Chicago, I got a chance to stop by Navy Pier and get another "voyage" with the good people at Tall Ship Windy. A group of us jumped on and completely enjoyed about an hour of beautiful views of gorgeous Chicago. CONCLUSION There are several boat tour options in Chicago, but I enjoy the hokey and fun style of Tall Ship Windy. 5/5 RECOMMEND ***************ORIGINAL REVIEW*************** ************************************************* BACKGROUND I pretty much love everything about Chicago, but going on an afternoon sailboat tour of Lake Michigan with a bunch of work colleagues instead of being at the office, is definitely a highlight. A group of six of us decided we wanted to spend the afternoon on the lake, so we met last minute at Navy Pier. We had zero clue what we were looking for, so we walked up to boats and asked their schedules and costs. There wound up being a range from $10 to $1,000's, depending on what type of cruise, the length of the voyage, and type of boat. The next available shorter and cheaper, fun cruise that was available, was the Tall Ship Windy. TALL SHIP WINDY: THE HISTORY Tall Ship Windy is a 148 foot traditional four masted gaff topsail schooner. The ship is built with modern materials, however, like old trading schooners and sail training ships, the Windy has all the character and charm of the great Age of Sail. Windy was built by Detyens Shipyard, Inc. Windy was welcomed as the biggest and newest schooner to the Lake Michigan Fleet in 1996. TALL SHIP WINDY Tall Ship Windy has several different tour options: 1. Lakeside Architecture: Which sails across the lake front looking at prominent architecture, which comes with a history lesson of historical maritime roots to modern science and technology. Children up to 12 $10 / Adults $30 2. Real Pirates of the Inland Seas: True stories of piracy on the Great Lakes. From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. Children up to 12 $10 / Adults $30 3. A Sailor's Life For Me! This is a trip through time, hear the story of how Tall Ship sailors became sailors, where on the earth they sailed, and what they did on these great ships. See and touch their tools of trade, discover how they lived every day, and what made Tall Ship sailing on the Great Lake "Great!" Children up to 12 $10 / Adults $30 4/5. Wednesday & Friday Nights Fireworks Cruises! Special Event Sail! Grab an adult beverage and lay back and watch the firework display as you cruise around the Chicago Skyline. Children up to 12 $20 / Adults $34.50 6. Haunted Harbors: Spooky storytelling adventure peers into the dark waters of the Great Lakes ghost ships and the darker deeds of souls that sailed it's shoreline. Children up to 12 $10 / Adults $30 CONCLUSION We picked #3 A Sailor's Life For Me! It was super hokey, and really fun. The crew got convincingly into their character roles and they're very knowledgeable about the history. It was quite interesting. The sun was setting and the Chicago skyline looked perfect. The whole trip was 75 minutes long. Absolutely a wonderful way to spend an afternoon. 5/5 RECOMMEND OF NOTE *Make sure to check out the lineup of Special Events, Private Charters, Educational Charters, Weddings, and Group Sails. *There are also gift certificates available. *The next season starts May 2016. *For more information: https://tallshipwindy.com read more

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

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

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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Ahoy Mateys! Right on Navy Pier is a pirate ship, but that ship is a boat ride themed to pirates. It's quite an enjoyable experience. There are different times which are for different things to learn. I went on the boat ride for architecture. Also, the captains of the boat will ask for volunteers to raise the flags! Also, I never knew some stuff the captain said. It was very interesting. The views are fantastic. You can see a lot of what Chicago has from the boat! Don't forget that there is a bar on the ship! The captain was really good. He had a nice presentation, and had a great speaking voice! Plus, he felt like a pirate! All in all, great boat ride that you shouldn't miss! I will come back soon. read more

Tall Ship Windy - The view of some of Chicago's buildings. Fantastic! - Boating Near Me - Chicago, Illinois

Take it from me: Don't wear a skirt. Other than that, a fun experience. Great views of the city. Even better views if you wear a skirt. 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

We embarked on a Saturday 7 pm cruise aboard the Windy and after having read some of the other reviews, I didn't know quite what to expect. So I'm happy to report that it turned out to be a fun and relaxing sail on a beautiful summer evening. When I saw the crew dressed as pirates I thought, oh no, is this going to involve audience participation? But it didn't. Your cruise can be as interactive as you want it to be. You can kick back and relax on the upper decks and you'll be left alone or you if you want a little more action, you can sit on the center deck and listen to the pirates tell and act out stories. They also let kids help raise the sails (which I can imagine would be a cool experience for any kid). For those reviewers who found it underwhelming, lighten up! It's a sail boat, not a speed boat. And it's sailing not a roller coaster ride. Cruise time of an hour was perfect and we went out as far as the Chicago Harbor lighthouse, enjoyed beautiful sunset views of the Chicago skyline, and even picked up a lovely breeze. Crew was very friendly--a guy named Orion was the star of the boat and there were a few young, charming Irish lads here from Ireland for the summer to work on the Windy and one of its sister boats the Red Witch. FYI, you can book the Red Witch for private parties and themed parties. Said charming Irish lads will dress up as pirates if you want them to--I know because I asked! Arrrrrr! I'm glad I got the Groupon for $18 because I definitely wouldn't have wanted to pay the regular price of $35 for this cruise. Non-prime time tickets for sailings before 3:15 pm are cheaper at $24. If you go, I'd recommend going in the daytime so you can actually see the lake and other scenery. If you're looking for something on the lighter and more casual side, versus a textbook architectural tour, you'll enjoy the Windy. read more

A great activity for all especially with kids. It is the only boat with the masts/sails out of all touring boats along the navy pier. Pick a nice day and come out sailing.... It was spacious on the ship. There were plenty seats on the bench or on the top of huge wood storage boxes. There is an open area for the captain which was super cool as we could watch how the captain maneuver the ship. The staff on the ship was energetic and friendly. My son was excited when they asked his help to raise up the pirate flags. Shortly after we left the pier shortly, the captain ordered the staff and kids raise up the massive sails. That was really thrilling part for old or young kids. The ship didn't sail too far to the south side of the lake from the pier, not even the museum park. We were facing the gorgeous view of Chicago skyscrapers from the lake. While a pretty pirate gave us the history of Chicago and funny stories, I was just enjoying the breathtaking view. It was a bit cool on the ship as it was in mid of 70f. One of the pirates was so kind to get some blankets for us to keep us warm. The captain actually invited one boy to take the control of the big wheel for a few minutes. Very cool. Before we realized it, the ship was approaching back to the Navy Pier. We all loved the tour. It is different that the Chicago river one which you will see lots of buildings and hear the stories about this. It is more kids friendly with a great view from the lake. I have got the Groupon so it is half off for the adult ticket which is a great deal. read more

Wow, upon reading some of the negative reviews we ALMOST didn't go yesterday, luckily I decided to overlook it & went anyway... The outcome: We had so much FUN!!! It was GREAT!!!! Our host/Pirate was named Orion & I can't praise this guy enough! He knew all the historical facts & really truly seemed to love what he was doing. With a wonderful mix of humor, history, a fantastic sail boat ride & the gorgeous Chicago skyline it made for a perfect & worth while outing. I would also like to mention that the crew was helpful, courteous & extremely friendly. We got to raise the sails, there were PLENTY of seats, they provided blankets & everyone seemed to be having a blast! I can't wait till next spring to go back again!!!! I WOULD 100% RECOMMEND THE TALL SHIP WINDY!!!!!! :) read more

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[insert the obligatory "I'm on a boat" joke. Except you are not on a boat. You are on a ship. A tall one. One that has pirates?] Sailed the high seas (cough lake michigan) for a professional event, so I can't comment on their normal pricing or themed adventures. But I can tell you that when its a beautiful Chicago summer evening, there is no better place to view the skyline, watch the sunset, and have a few drinks than on a massive sailboat. 75minutes was the perfect time to eat, drink, and mingle. While you don't go very far from Navy Pier, that's to be expected in that time frame. And the city is breathtaking regardless. A few complaints: -we can do without the fake pirate accents. Kids like it. A boat full of female attorneys does not. -Near disaster happened when the ship did not have white wine (see "boat full of female attorneys," supra). Thankfully Bluebeard came to the rescue at the last minute. For a fresh take on an event venue, I'd check it out. read more

Tall Ship Windy - Boating Near Me - Chicago, Illinois

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