Chicago Skyline Tall Ship Sightseeing Cruise
Chicago, USA
Chicago Skyline Tall Ship Sightseeing Cruise
Badge of Excellence
Chicago, USA
- 1 hour 15 minutes (approx.)
- Offered in: English
Overview
What's Included
Meeting and Pickup
Itinerary
Additional Info
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.5
based on 514 reviews
Amanda_S, Nov 2024
The crew involves the guests. Either seat back and enjoy or volunteer to help bring up the sails. Excellent for a relaxing, beautiful time away. All ages would enjoy
Response from Host, Dec 2024
We are glad you enjoyed all the aspects of our charters and hope you will join us next season for more fun!
Anna_Y, Sep 2024
This is a tourist activity, but on a warm day, you get an hour plus of cool breezes, gorgeous views, and relative quiet.
Response from Host, Sep 2024
Glad you enjoyed your time aboard with Windy!
Mirela_S, Sep 2024
Excellent choice for a very unique experience. The whole crew is fantastic.
The Captain, the guy from Whitefish Bay and lady from Illinois, all wonderful people.
The sunset cruise is beyond description. Skyline at night is surreal. A MUST SEE.
Hope you enjoy it as much as we did.
Response from Host, Sep 2024
We do love the magical sunset charters, different and majestic view of the skyline from Windy!
SHEILA_A, Sep 2024
Disappointed with trip - as advertised as leisurely trip around Lake Michigan on a full on schooner in full sail .
In reality the schooner motored just beyond breakwater where it anchored and 3 sails were raised but didn’t actually “sail” anywhere . Sat there for an hour then sails taken down and motored back to port .
The advertising clearly shows the schooner with full sails up leaving the harbour and description promised a relaxing sail .
Response from Host, Sep 2024
Thank you for letting us know. I’ll speak with the Captain directly.
Mackejo_h, Sep 2024
Highly recommend ! Staff were extremely friendly and fun! A very relaxing way to spend the evening watching the beautiful sunset
Daniel_R, Sep 2024
Very nice and pleasant tour. Staff was great and there was no unnecessary talk while sailing. I wish they would’ve gotten closer to the shore to better see the skyline.
Response from Host, Sep 2024
Thank you for joining us and glad you enjoyed your time on board. We are restricted by the waters depth on how close to shore we can get, but we can always try to create a charter to meet that request!
Dan_P, Sep 2024
The most memorable moments for me was the gorgeous weather on this day, the chicago skyline, the relaxing boat ride and celebrating my 24th Anniversary with my wife on this tour. Oh the cannon being shot off was cool as well.
Response from Host, Sep 2024
Thank you for sharing your 24th anniversary with us!
We hope to see you on your next big celebration!
Steven_A, Sep 2024
Very nice experience today. The weather was perfect for it. The crew was entertaining and learned some history, too! Good job!
Response from Host, Sep 2024
Glad you enjoyed all aspects of being on the water with us!
Raymond_M, Sep 2024
This was a fun Cruise out on the lake with great views of the city. This was very fun, enjoyable, and relaxing.
Response from Host, Sep 2024
Woo Hoo! Thank you!
Kari_K, Sep 2024
It was a beautiful day, and it was fun but it is really short, they say it is 1 hour and 15 minutes and that you need to get there 30 minutes before your departure time. We didn’t board until 5 minutes before and 30 minutes is going out and coming back in so you are really only sailing for about 30 minutes.
The fun facts/ architecture was interesting, but they could lose the whole pirate thing, it’s a little corny!
Response from Host, Sep 2024
Thanks for your feedback
Karen_C, Sep 2024
I booked this trip for my husband’s birthday not knowing that it was the Pirate and Mariner tour.
Our adult daughter was with us and we had a blast!! The crew was so fun and welcoming! It was a windy and beautiful afternoon and we enjoyed some adult beverages and snacks from the bar. We learned a lot about pirates on Lake Michigan. And honestly, when they were telling the pirate stories it was just on the main deck and the microphone was off. So if you would prefer to just enjoy the boat you can move to another deck. It was a fantastic experience to see the Chicago skyline from the Lake. I would highly recommend this tour!
Response from Host, Sep 2024
We are glad you enjoyed your time on board with us for our Pirate Stories (and Lore)! We hope you'll join us again for more fun tales and history!
Douglas_M, Sep 2024
Beautiful views, very entertaining “pirate” speaker. Would do this again. We loved it. Bar in the lower level and items to buy.
Response from Host, Sep 2024
We do have some great Pirates on board and some tasty Rum drinks to make the entire experience memorable!
Kameela_D, Aug 2024
Windy’s crew were very adamant on giving their guests a hands on, memorable experience. The ship’s narrator was very enthusiastic and entertaining during the tour. Overall a great experience! Would definitely recommend
Response from Host, Sep 2024
We do like to offer an experience that is hands on for those that wish to hoist the sails and fire the cannons! Or you can simply sit back and enjoy to skyline!
Anthony_B, Aug 2024
I thought the ship was nice and the view was great. The boat doesn’t go fast so I think everyone could enjoy it. The staff were friendly.
Response from Host, Aug 2024
We are glad you enjoyed your time aboard with us and hope to see you again!
Denise_G, Aug 2024
Enjoyed conversations with Captain Rodney and crew. True sailors with knowledge and experience to share.
Response from Host, Aug 2024
Thank you! Rodney loves Windy and we are glad you enjoyed your time on board!
Codi_C, Aug 2024
Was deciding between this skyline tour and one of the architecture tours- so glad we chose this one!! The boat staff are lovely and generally happy to be there! There’s some hands on activities little ones (and adults) can help out with on the ship 10/10 would recommend getting out onto lake michigan for a cruise with these guys!!
Response from Host, Aug 2024
Thank you for your kind review. Our Crew do work hard, but LOVE what they do; so I'm glad it shows!
We hope you'll join us for more fun on a different charter!
Angel_N, Aug 2024
Raising the sails and architect stories from the staff. Mostly enjoying Lake Michigan beauty and the Chicago Skyline.
Response from Host, Aug 2024
We are glad you enjoyed your time on board with our fabulous crew and hope you'll join us again!
MCLARKE320, Aug 2024
Great experience! Fun time! Beautiful sunset. The crew of the Windy and Captain Rodney were awesome! Highly recommend!
Response from Host, Aug 2024
We’re so glad you had fun! Thank you for sailing with us, come SEA us and Captain Rodney again!
LisaB, Aug 2024
The actual tour itself was good. The crew were nice and the views were great. It was a nice day and we went out on the 7:00 tour, so it wasn't hot or too sunny to see.
The only thing that put a damper on the experience is that we arrived an hour prior to the start time to ensure that we were on time and we're able to get a good seat. Unfortunately, we sat down to enjoy a beverage at the first bench for their shop, which is also where the ships gangplank is. We had no idea without that 50 feet past the gangplank (on the other side of a landscaping feature) is actually where the line begins. Therefore, instead of being near the front of the line, we were among the last to board and all of the best seats (on the bow and aft) we're full.
While we were sitting there, the crew were walking around preparing the ship for the next run, so we could have asked if we were in the right place, but there was nothing to indicate that ticket holders would line up so far away from what appeared to be their main entrance. Adding a sign to indicate where the line begins for boarding would be really helpful to first time passengers and avoid the loss of stars in reviews for what is essentially an administrative issue.
Response from Host, Aug 2024
Thank you for joining us and we are glad you enjoyed your time on board and it sounds like you were right there in front of the queue. We do have seven different signs along the ropes that indicate where we begin queuing up and regret that you missed them. We also offer a VIP queue (that is also clearly marked) for guests that purchase the VIP tickets. We will definitely look into adding more signage to guide our guests to the line.
Ruben_H, Aug 2024
If was super nice. Unfortunately, it was too windy and we could not leave the harbor but the views of the Chicago skyline from the water are incredible
Response from Host, Aug 2024
We are glad you enjoyed the views!
Maria_d, Aug 2024
The crew was nice and made people feel welcomed. Thank you very much, I'll gladly recommend this experience to anybody visiting Chicago.
Response from Host, Aug 2024
We are glad your time on board was welcoming and fun!
Allison_W, Aug 2024
Loved the boat ride, very peaceful. Only negative is the gps location it gave was on the wrong side of the pier. If we had not asked a security guard we would have been waiting and missed the whole thing.
Response from Host, Aug 2024
We are glad you found us and we will look into our Google location.
Jane_N, Jul 2024
The crew was dressed in a seafaring way. It was engaging to watch them work and to have an opportunity to hoist sail. The music was fun. The skyline was so beautiful at sunset. Drinks were good. Loved the trip.
Response from Host, Jul 2024
EXCELLENT! Hoisting the sails is always a fun aspect of the charter (but it IS harder than it looks!) Glad you enjoyed your time with us!
Chris_C, Jul 2024
The skyline was beautiful from the water. The crew was entertaining and involved the guests with sailing preparations.
Response from Host, Jul 2024
We hope you had a chance to hoist the sails! It's a workout in itself! Glad you enjoyed your sail and we hope to see you again!
james_c, Jul 2024
Fun and interesting sail out onto Lake Michagan. Great to see Chicago from the lake. The narritive was also interesting. Very relaxing after a long day of walking. The fact that the weather was perfect helped even though the operator had nothing to do with thath LOL. But definately recommend
Response from Host, Jul 2024
Glad you enjoyed the sail, the city and the weather!
jason_r, Jul 2024
Great experience and the crew was excellent!! We enjoyed the view of the city and the 1800’s sail experience!!
Response from Host, Jul 2024
So glad you had fun! Our crew work to make your time on board both memorable and safe! We welcome you back anytime!
Linda_C, Jul 2024
The tour guide and shipmates were fun and knowledgeable! The boat is beautiful. I’d recommend this. It was a solid good experience.
Response from Host, Jul 2024
Thank you! We hope to see you another time when you are in town!
Elisha_Y, Jul 2024
We enjoyed the ride. Helping to set the sails. Learning about pirates. We had a group of 59-5 years old and everyone enjoyed the ride. There are drinks and snacks on the boat.
Response from Host, Jul 2024
Happy that everyone enjoyed their time on board and thanks for helping hoist the sails. Always fun!
khamburg1, Jul 2024
Great crew and fun trip. We took the pirate themed cruise and one of the pirates told us a story about a pirate in the past. There is also some participation helping to raise the sails. It was much less expensive to book via Viator than to do so on the Windy site. Just sayin'.
Response from Host, Jul 2024
We are glad you enjoyed your sail with us!
Gerald_J, Jul 2024
Guide was great!! Just the right length of tour. Will take other out of town guests on your various tours
Response from Host, Jul 2024
We look forward to having you aboard again!
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