Chicago Skyline Tour: Scenic Sail on Official City Tall Ship
4.5
482 Ratings
Chicago
Experience the beauty of Chicago's skyline on a scenic sail around Lake Michigan. Discover the city's architectural wonders and enjoy breathtaking views from the Official Ship of Chicago.
Duration: 1 hour, 15 minutes
Cancellation: 1 day learn more
Highlights
  • Navy Pier - Departs from the historic Navy Pier, one of the most popular tourist attractions in the city.
  • Lake Michigan - Sail on the third-largest of the Great Lakes. Lake Michigan is itself a natural wonder.
What's Included
  • Local taxes included
What's Not Included
  • Alcoholic, Non-Alcoholic Drinks & Snacks (available for purchase)
  • Gratuities
  • Hotel pickup and drop-off
Additional Information

Escape the vigorous city life! Journey around Lake Michigan and experience the exquisite shoreline of Chicago at your own pace. Marvel at the globally renowned skyline, witness breathtaking views, and uncover the aquatic side of the Windy City. The Official Ship of the city, Windy, measuring at 148 feet in length, prides itself as one of a handful quartet-masted Schooners constructed within the United States. Recline and relish a soothing cruise aboard an authentically historical watercraft. Choose from our Pirate and Maritime Stories Sail at 1pm, Skyline/Architectural Theme Sails at 3pm and 5pm, or the Skyline Sunset Sail at 7pm.

Our sail lasts for nearly 75 minutes. The ship embarks punctually at the slated time, so we advise you to account for possible parking time, off the pier if need be.

  • All Passengers must be present 30 minutes prior to advertised sail time. The Ship leaves on time. Please allow ample time for Chicago traffic, getting lost, and not being able to park close.
  • Minimum drinking age is 21 years
  • Dress code:should be sensible for the weather
  • Children under 16 years of age, must be accompanied by an adult
  • Windy is NOT HANDICAP accessible.
  • Guests must be able to ambulate up and down 6 steps on each side of the boarding ladder.
  • Assistive devices must be left on the dockside storage area and may not be used on the ship while underway.
  • Windy is NOT HANDICAP accessible
Location
600 E Grand Ave
East Grand Avenue
We are located on the South dock, on the south side of Navy Pier, immediately in front of the Billy Goat Tavern. If walking on the south dock from the entrance, walk where you see restaurants and boats, walk pass the Ferris wheel, walk past the sign for the Shakespeare theater, then on right!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.5
(482 Ratings)
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Bethanyb975
Aug 3, 2024
Worth every minute every penny great experience - The ship was amazing very beautiful very well-kept the crew very entertaining and very knowledgeable of the history of Chicago captain there's nothing bad I could say about him she was very good it was a beautiful day at sea. Great experience all around would definitely do it again oh and it was safe because I was by myself.
Review provided by Tripadvisor
Venture48640189093
Jul 30, 2024
Amazing and romantic. - Amazing and Romantic. Great vibes on the water overlooking the skyline of Chicago. Crew was amazing and interactive..
Review provided by Tripadvisor
693deannar
Jul 29, 2024
Highly Recommend - This was a really fun experience with my daughter! The crew was amazing and the view of the city beautiful. Highly recommend.
Review provided by Tripadvisor
Jane_n
Jul 28, 2024
Sailing with the crew on a Tallship. - 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.
Review provided by Viator
Christophe
Jul 28, 2024
Loved it. - We had a great experience. It is good to feel the quietness. Great team, especially Andy, great speaker and impersonator.
Review provided by Tripadvisor
Chris_c
Jul 23, 2024
Great sailing experience! - The skyline was beautiful from the water. The crew was entertaining and involved the guests with sailing preparations.
Review provided by Viator
James_c
Jul 23, 2024
Great sail on the late - 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
Review provided by Viator
Jason_r
Jul 23, 2024
Great experience and the... - Great experience and the crew was excellent!! We enjoyed the view of the city and the 1800’s sail experience!!
Review provided by Viator
899karinh
Jul 17, 2024
Fun time with pirates! - Fun trip with the crew dressed like pirates (well, some of them). One pirate told a story that was quite interesting. Several folks (and a few kids) helped with putting up the sails. This was an anniversary event for us and we were afraid the ship would be overrun with kids but it wasn't -- maybe 3 or 4 well-behaved kids were on board. Overall, a great trip. I suggest you buy tickets on Viator because the ship itself adds all sorts of taxes and fees making the price much higher. Viator does not.
Review provided by Tripadvisor
Allison_w
Aug 3, 2024
Great boat ride - wrong GPS location - 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.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1 Adult
August 2024
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