Tall Ship Windy

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 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 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
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.
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:
I ⁵⁄₅ highly recommend Tall Ship Windy Boat Tours!

Every year we host a series of client events in Chicago and one of the days is «Family Day», where our clients have the opportunity to bring their spouse, children, grandparents, etc. to the event. This year we decided that we wanted to tie the experience to a pirate theme, so we chartered the Tall Ship Windy and it was a perfect choice! The crew were «in character» with their pirate garb, extremely expressive telling pirate stories… arggggh!!!, engaged our guests to partake in hoisting the sails and even participated in some jousting with the kids with balloon swords they blew up just for them. I am not sure who had more fun… the kids or the crew, but an absolutely fantastic time was had by all!
This is a family run business and you can tell that they take good care of their associates! I would not hesitate to recommend Tall Ship Windy to anyone! It was such a memorable experience that we are considering doing this annually! Hats off to all with Tall Ship Windy for a job well done!

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.

we had an awesome time. I liked the fact that the crew was well trained and the talented host knew good stories to tell. very entertaining. I don’t usually give review but for this experience, I just had to.
the only weird thing was there were only two ppl dressed as Pirates…
Definitely gonna go again.

This was such a memorable experience! This was our 2^nd 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.

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.

This rating is not for the experience. It’s for the fact that they charge $ 10 for a baby to board. I have never been to an attraction that charges for a child under 2. I find it ridiculous. I’m still contemplating whether I want to pay. Will definitely update the post if I do.

My sister & I went on A Sailors Life for Me tour and had a blast. Our tour guide Gilligan was AMAZING and very animated & informative. He truly made our experience one to remember. I definitely recommend Tall Ship Windy for a different kind of tour in Chicago. It’s family operated and the entire crew was wonderful. Gilligan… I million thank you’s for being so AWESOME!!!

The crew was fun! Loved the ride. We went down for the Wednesday fireworks. It was so worth it! It is a family owned operation. There is a nice little bar on the deck. Planning to go to one of their amazing theme events next!

Outstanding sail along the city coastline with an informative and humorous description of the skyline. Helped raise the sails! Great crew.

This was a fun experience for me and my little brother — I tend to get sea sick, but did ok on the top deck. My little brother loved the opportunity to listen to pirate stories and watch the cannon be shot.
I was hoping for a little bit more piratey atmosphere, but all in all it was a good trip.
A shout out to Ben the pirate as he stated he reads these personally!

Set sail at 7:30pm. Spectacular sunset and view of the Chicago skyline. Crew was great. Smooth sailing. Highly recommend!

Let me tell you all the fantastic things about this tour:
Fun Crew– they obviously have fun and enjoy what they are doing. I was free to roam the ship as I pleased which was nice. They even let you help them out with the sails. #piratestatus The guide was knowledgeable and easy to listen too.
The Bar– fits right into the theme. Pirate’s punch was VERY tasty and worth spending double in my opinion. The boat was never rockin to hard for a full drink! Snacks were available too.
Location– Navy Pier… duh of course its great.
some other things:
family friendly, great skyline view, really great photo ops. Go check it out!

Gord and I did the 7:30pm sailing on the Tall Ship Windy. It was about $ 30 each and was about 75 minutes.
The theme was «Real Pirates of the Inland Seas»
We sat in the front (the bow).
You could help raise the sails.
Ben the Pirate told stories.
The views were great and the sunset was fabulous.
Gord and I love going on boat cruises and this one had the added bonus of the sunset.

Fantastic for families and friends alike. Crew and captain are fun and knowledgeable.
Fun Lake Michigan Pirate stories after the kids help raise the main sails.

Drinking on a moving boat is not a good idea if you get sea sick. My girlfriend insisted on going, because her work friends were going. I have not wasted 40 bucks more effectively than I did today. Reader deal. So she got to go for free from referrals. Sea sick. Girlfriend mad I’m sea sick. I dislike beer, waves, and basically this experience. Staff incredibly nice. Because they have sea legs. This is torture.
Paid to leave at 8. Leaves at 820. Unlimited beer I don’t want. Staff eating food 30 minutes before guests. Limited food as well. It’s a damn trap.

I love taking my visiting family and friends on the Tall Ship Windy when they come to Chicago. I recommend the afternoon sail — great way to see the city and skyline. Crew is fun and if you want to help hoist the sails, then jump in when they ask for volunteers! Tour is 75 minutes and a perfect relaxing way to spend the afternoon.

Tall ship windy was a great experience. We were a group of 5 and we had no plans at the navy pier. We saw the tall ship which looks great and unanimously decided to go for a ride. Everyone from the ticket salesperson to the crew were friendly and always carried a smile. The host/​greeter introduced himself as Gillighan and he was extremely energetic and entertaining. We sat in the back of the ship where the captain was. He was a really friendly guy and let us all take pictures with the steering wheel. Meanwhile, Gillighan was entertaining the kids with stories, on the deck. I highly recommend Tall Ship Windy. They offer something for everyone. Kids have stories, young adults have a bar and a fun crew to talk to, couples have the beautiful chicago skyline and older adults have a nice, quiet and serene experience. Keep it up guys! I’ll visit again.

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?

Okay, I have boarded this ship with Pirates.
If you don’t hear from me for awhile please come and fish me out of Lake Michigan with a big net!
So, every Summer I have a Ritual where I take a Boat Ride along
Lake Michigan, but, this year I wanted to try something a bit different
so I being the Daredevil and Excitement Seeker that I am decided to
board a ship with Pirates…
Now, I must admit that I was hoping for some Mutiny on the Bounty,
some at Sea Mayhem, even some Choppy Waters.
I boarded this Pirate Ship at 10:45 am this past Saturday for an
Architectural Tour, and the not so mean Pirate Guy narrated some
interesting facts about some of Chicago’s Buildings and Architecture.
And, he was quite the charming host, I mean this guy was dressed in
like a Velvet Overcoat and boy was it humid on the lake on Saturday!
So, I sat on the top deck watching all the birds/​seagulls and we sailed
off onto the lake for a bit, and honestly this boat ride was so smooth and
peaceful, what’s up with that?
I boarded a boat with Pirates, I wanted some excitement, or maybe
even the boat to tip over since we were told they had enough life
jackets on board for everyone…
But, alas, no such luck for it was a lovely cruise around the lake,
I took some great pics of the city skyline and of some Pirates!
Seriously, if you are looking for a great way to spend 75 minutes seeing
Chicago’s Skyline and like a calm, peaceful ride this is definitely the
ship for you to set sail on.
However, since I am a thrillseeker, my next ride will be on the Speedboat
Seadog.
But, Big Props to the great staff of people on the Tall Ship Windy.
They Rocked!
Unfortunately, the Ship did not…