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Boxing (Wrigleyville)Chicago Skyline Cruise
What to expect
- Enjoy Chicago's beautiful skyline from a unique vantage point
- Take a leisurely trip around Lake Michigan on a sailboat
- Relax with the wind at your back and gentle waves rocking you back and forth
| Date | Start Time | Duration | # Spots | Price |
|---|---|---|---|---|
| Mon, Jul 24 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Jul 24 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Jul 25 | 7:00pm | 75 min | 10+ | $30.00 |
| Tue, Jul 25 | 9:00pm | 75 min | 0 | $30.00 |
| Wed, Jul 26 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Jul 27 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Jul 27 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Jul 28 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Jul 28 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Jul 29 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Jul 30 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Jul 30 | 9:00pm | 75 min | 10+ | $30.00 |
| Mon, Jul 31 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Jul 31 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 1 | 7:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 1 | 9:00pm | 75 min | 10+ | $30.00 |
| Wed, Aug 2 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 3 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 3 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 4 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 4 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Aug 5 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 6 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 6 | 9:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 7 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 7 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 8 | 7:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 8 | 9:00pm | 75 min | 10+ | $30.00 |
| Wed, Aug 9 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 10 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 10 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 11 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 11 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Aug 12 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 13 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 13 | 9:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 14 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 14 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 15 | 7:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 15 | 9:00pm | 75 min | 10+ | $30.00 |
| Wed, Aug 16 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 17 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 17 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 18 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 18 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Aug 19 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 20 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 20 | 9:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 21 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 21 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 22 | 7:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 22 | 9:00pm | 75 min | 10+ | $30.00 |
| Wed, Aug 23 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 24 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 24 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 25 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Aug 25 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Aug 26 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 27 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Aug 27 | 9:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 28 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Aug 28 | 9:00pm | 75 min | 10+ | $30.00 |
| Tue, Aug 29 | 7:00pm | 75 min | 0 | $30.00 |
| Tue, Aug 29 | 9:00pm | 75 min | 0 | $30.00 |
| Wed, Aug 30 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 31 | 7:00pm | 75 min | 10+ | $30.00 |
| Thu, Aug 31 | 9:00pm | 75 min | 10+ | $30.00 |
| Fri, Sep 1 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Sep 1 | 9:00pm | 75 min | 10+ | $30.00 |
| Sat, Sep 2 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Sep 3 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Sep 3 | 9:00pm | 75 min | 0 | $30.00 |
| Mon, Sep 4 | 7:00pm | 75 min | 10+ | $30.00 |
| Mon, Sep 4 | 9:00pm | 75 min | 0 | $30.00 |
| Fri, Sep 8 | 7:00pm | 75 min | 10+ | $30.00 |
| Sat, Sep 9 | 7:00pm | 75 min | 10+ | $30.00 |
| Fri, Sep 15 | 7:00pm | 75 min | 10+ | $30.00 |
| Sat, Sep 16 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Sep 17 | 7:00pm | 75 min | 0 | $30.00 |
| Fri, Sep 22 | 7:00pm | 75 min | 0 | $30.00 |
| Sat, Sep 23 | 7:00pm | 75 min | 10+ | $30.00 |
| Sun, Sep 24 | 7:00pm | 75 min | 0 | $30.00 |
| Fri, Sep 29 | 7:00pm | 75 min | 0 | $30.00 |
| Sat, Sep 30 | 7:00pm | 75 min | 0 | $30.00 |
| Sun, Oct 1 | 7:00pm | 75 min | 0 | $30.00 |
Book now
Select a time slot to book (212) 858 9559About this Activity
Key Highlights
| Price | $30.00 per guest |
| Duration / Session | 75 min |
| # Sessions | 1 |
| Rating | 14 positive reviews |
Cancellation Policy
Reviews
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Ian S.
A Sailor's Life for Me! Tall Ship Experience September 13, 2015Loved it!
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Galen G.
Real Pirates of Lake Michigan Tour October 6, 2013Rick was an amazing storyteller, glad we picked the Real Pirate cruise, probably the best experience I've had on Navy Pier, I felt like I actually learned something about the Great Lakes history. Tell your friends!
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alfie2u .
Real Pirates of Lake Michigan Tour September 6, 2013The cruise was great. When I got there I found that there were three different places that you can sit. The front end, the middle and the back end. If you want to sit on the ends make sure that you are in the front of the line and quickly make your way to either end. Those seats fill up fast. The middle is a good place to sit as that is where the shows and presentations are taking place. On our cruise our pirate had different items and told us how they were used by pirates back in the day. Next at the beginning of the cruise they will ask for volunteers and that is to help raise the sails. If interested get up and do it. It looked like fun. After the sails were up and we were away from Navy Pier the engines were turned off and we were sailing with the wind. It was very quiet and relaxing. We had great views of the Chicago. Eventually we made it back to Navy Pier. It was a very nice and relaxing ride. Finally, if you have kids bring them along as the crew and our pirate host was great with them. From what I saw we all (kids and adults) had a lot of fun
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LaurLaw .
Chicago Skyline Cruise August 12, 2013What a great program to be able to sail on a tall ship and experience the views of the Chicago skyline. I was fortunate enough to be onboard for the fireworks and I feel like we had the best seats in the house. There is a bar available with drink purchases and the entire crew is enthusiastic. The Captain is friendly and available for questions. Highly recommend.
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Starfish738 .
Real Pirates of Lake Michigan Tour July 31, 2013I just got back from my first trip ever to Chicago. I took my 17 year old daughter and while we did several fun things, The Tall Windy pirate ride with Pitate Rick was at the top. I was enthralled with each of his true pirate stories. I loved his passion for the stories and his delivery made it all so much fun.
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Jae H.
Lakeside Architecture Sail July 25, 2013I'd like to start off my saying that tall ship windy is perfect for people with children. Not only does it offer the classic architecture tour, it also offers themed events. The name of the tour I went on was something like "real pirates". An employee dressed up like a pirate told stories on the main deck. People not interested on the stories were able to go onto one of the upper decks to relax.
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Melissa S.
Real Pirates of Lake Michigan Tour July 14, 2013Our whole family had a wonderful experience with tall ship windy. We took the pirate excursion and pirate Rick was phenomenal. He was entertaining, informative and fun for adults and kids alike. My husband and I along with our 7 and 4 year old alike had a lovely afternoon. He even "coded" information so the adults understood but kids were not impacted by violent pirate imagery. Perfect! We even bought the touristy photo at the end as a memento. We will definitely sail again with tall ships windy:)
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Ashley C.
Chicago Skyline Cruise June 27, 2013We sailed on the Windy today and had a fabulous time! The entire crew were amazing and really catered to the kids on the ship showing them sailing skills and allowing them to participate.
The views of the city skyline were beautiful and the ship was clean and safe. I highly recommend this trip if you are visiting or a local! -
Sandra L.
Real Pirates of Lake Michigan Tour June 21, 2013Took a Pirate cruise on the Tall ship Windy yesterday. We had a great time! Pirate Dave was very into his role and job. He was entertaining and also full of facts about life on the high seas of Lake Michigan. A bar was also on board,limited,but a nice perk and also a"head" if you needed that. The ship was smooth sailing and they even offered us blankets to ward off the lake chill. The crew was very gracious and friendly. They even gave us back our tickets to use at a later date for a half price cruise. It was a beautiful,sunny day and had great views of the city and the lake itself. I would recommend this tour to vacationers and Chicagoans like me!
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Sandy G.
Real Pirates of Lake Michigan Tour June 14, 2013I took my 9 yr old niece on the pirate sailing. We both had a great time. The boat left on time and the Crew were professional and endured all had a great and safe time. They made sure all the children were included in the pirate takes and actually had the kids act out scenes. Great outing on a sailboat with beautiful Chicago views.
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Donna J.
Lakeside Architecture Sail October 2, 2012Loved being on a tall ship. Even got to hoist the sails. It was a beautiful September day so there was plenty of wind. Loved seeing the city from the Lake. Tour guide was great but I'm glad I did the architectural boat tour first. It wasn't always easy to know which building was which.
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Susan F.
Real Pirates of Lake Michigan Tour October 1, 2012Went on the Friday night Pirate cruise. Being a local, wasn't expecting much at Navy Pier. Had a beer at Billy Goat instead of waiting in line. Was entertained by the stories of the Great Lakes pirates and a couple beers. A little chilly, but they provided blankets. Overall, a good way to start out the weekend!
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Alexander B.
Real Pirates of Lake Michigan Tour June 2, 2017Did not leave comment
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Quittman F.
Lakeside Architecture Sail August 23, 2015Did not leave comment
