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Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5302 reviews
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Chicago, United States
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

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Free cancellation
Up to 24 hours in advance. Learn more
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Safety measures
icon1 hour 15 minutes  (approx.)
iconOffered in: English

Overview

Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
  • Family friendly
  • See the sights day or night
  • Travel by boat and see the sights from the water
Saved to wishlist!
Local taxes
Alcoholic drinks (available to purchase)
Food and drinks (available for purchase)
Gratuities
Hotel pickup and drop-off
600 E Grand Ave , 600 E Grand Ave, Chicago, IL 60611, USA

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!

This activity will end right where it started.
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • 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
  • Service animals allowed
  • Near public transportation
  • Not recommended for travellers with back problems
  • 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
  • Travellers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 140 travellers
  • OPERATED BY Windy of chicago Inc, DBA: Tall Ship Windy
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What is the policy on face masks and attendee health during Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship?
A:The policy on face masks and attendee health is:

  • Face masks required for guides in public areas
See all safety measures taken by Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship.
Q:
What is the policy on sanitisation during Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship?
A:The policies on sanitisation are:

  • Hand sanitiser available to travellers and staff
  • Regularly sanitised high-traffic areas
  • Gear/equipment sanitised between use
See all safety measures taken by Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship.
Q:
What is the social distancing policy during Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship?
A:The policies on social distancing are:

  • Social distancing enforced throughout experience
  • Contactless payments for gratuities and add-ons
See all safety measures taken by Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship.
Q:
What measures are being taken to ensure staff health & safety during Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship?
A:The policies on staff health & safety are:

  • Guides required to regularly wash hands
  • Regular temperature checks for staff
  • Paid stay-at-home policy for staff with symptoms
See all safety measures taken by Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship.

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Reviews

4.5
star-4.5
302 reviews

Reviews by Viator travellers

We perform checks on reviews

Showing 1-10 of 302 reviews
star-5
Such a fun sail!
Cynthia_V
, Aug. 2022
Experience was great! The entire crew was very nice and welcoming. Loved the sail. Nothing beats those views. Thank you Sam for being so sweet and sharing neat Chicago facts.
star-5
Enjoyable Evening
Gregory_P
, Aug. 2022
Crew was engaging for the kids, recruiting them to hoist the sails. Beautiful evening on the water, with a unique perspective on the city.
icon Response from Host , Aug. 2022
We are glad you enjoyed your charter with us. We hope you'll join us again to hoist another sail and enjoy our skyline!
star-5
Fabulous tour.
Helen_M
, Aug. 2022
Wonderful story telling along with history. Polite and entertaining crew. My first time in Chicago - my friend, who is from Chicago, was so glad I chose this tour.
icon Response from Host , Aug. 2022
Welcome to Chicago! We are thrilled you enjoyed your charter with us and hope you will join us again next time you visit!
star-4
Spectacular sunset cruise
Michael_K
, Aug. 2022
This was a wonderful, relaxing Event. The weather was perfect and the view of the Chicago skyline at sunset was spectacular. I recommend looking for a seat on the aft deck near the Is wheel for the best views.
icon Response from Host , Aug. 2022
We are happy you enjoyed the views and the weather.
star-5
Rod & Bruce are the...
Natalie_C
, Aug. 2022
Rod & Bruce are the absolute best! They made our experience so much fun. Played great music, had amazing drinks & had an even better crew! 10/10 recommend 😊
icon Response from Host , Aug. 2022
Thank you! I love it when our Captains get involved with our guests, they are both a delight and valuable asset to our company!
star-5
An evening on Windy
Sue_M
, Aug. 2022
What a fabulous experience on Tall Windy! Beautiful memory. 🙏🏽 Crew did a great job! Thank you! Perfect weather.
icon Response from Host , Aug. 2022
Thanks! We love that you enjoyed your time with us aboard Tall Ship Windy and welcome you back anytime!
star-4
Great views and...
Jeffrey_S
, Aug. 2022
Great views and professional staff—although the host was obnoxious and and not humorous at all. He should tone it back or be replaced.
icon Response from Host , Aug. 2022
Thank you for sharing your thoughts! We regret you found our Pirate humor obnoxious and hope you'll join us again. "To Err is Human, to ARRRR is Pirate"~
star-3
The app didn’t work...
Nello_V
, Aug. 2022
The app didn’t work correctly. I couldn’t access my ticket with my phone. The Windy got me a ticket without the app.
icon Response from Host , Aug. 2022
Good Afternoon Nello Vignocchi, you may want to reach out to your booking agent Tripadvisor, as we the operator, have no control over the app. I believe your review is to Tripadvisor as we did accommodate you at the ticket booth to ensure you were able to join us.
star-3
Learning about the...
Christine_J
, Aug. 2022
Learning about the different parts of the sailboat. The crew was kind and skilled. I wish we would have actually moved out into the lake
icon Response from Host , Aug. 2022
We are glad you learned about the ship on our Educational charter! Join us for another charter where we sail further out.
star-5
Rare View of Chicago
Angela_F
, Aug. 2022
Interesting perspective of the Chicago Skyline. Andy provided unusually candid, entertaining commentary. Crew was equally engaging.
icon Response from Host , Aug. 2022
Thank you for writing, we love to hear we offer interesting perspectives and candid commentary! We strive to keep our charters interesting and glad you enjoyed! Please, join us again!
star-5
Wonderful fun experience
Debbie_K
, Aug. 2022
The weather is very unpredictable in Chicago summer. We waited until 4 pm to decide to go the this tour. It was great. Kids pulled up the front sail and it was an incredible experience. Nice city architecture story. Fun experience.
icon Response from Host , Aug. 2022
We do agree, the weather can be finnicky and it definitely can change within 15 minutes! We are glad you joined us and your kiddos got to experience the hoisting of the sails! Join us again next season for more fun!
star-5
Wonderful Sail!
Darrell_G
, Aug. 2022
First visit to Chicago. What a wonderful way to enjoy the lake and skyline! Beautiful! Would recommnend!
icon Response from Host , Aug. 2022
WELCOME to our beautiful city! We hope you'll join us again to experience more fun on the water, our incredible cuisine and spectacular venues!
star-5
Must do experience!
Kathryn_T
, Aug. 2022
Everything was amazing! The kids loved help raising the sails. The crew was knowledgeable and fun! The kids loved the pirate stories and the adults could actually enjoy it since the kids were being entertained. Absolutely amazing! What a blast for all 12 of us!
icon Response from Host , Aug. 2022
We love to hear this; especially that we entertained your large group! Please join us another time this season; the fireworks are Spectacular!
star-5
Schooner Wendy Ship Shape!
Mark_B
, Aug. 2022
We had a great time. It was laid back and the guide did a good job of pointing out the buildings and history of the Chicago skyline. I do wish I had brought my binoculars, though they were not necessary. Get on early for the seats on the front or back. There is a bar and gift shop in the hold. The crew was absolutely wonderful. Everyone was friendly and helpful. They put out the treasure chest for tips at the end. I normally don't like the pressure, but in this case, I had to show my appreciation.
icon Response from Host , Aug. 2022
We can't thank you enough for taking care of our hard working Crew! They do appreciate all gratuities and we appreciate you!
1 traveller found this review helpful
star-5
Fun weekend
Jerry_B
, Jul. 2022
Everything was Fantastic ! Staff very friendly ! My boys they’d loving it they said it was a good choice instead going to the river .
icon Response from Host , Jul. 2022
So glad everyone enjoyed their time aboard Tall Ship Windy! Join us again!
star-5
Perfect sunset cruise
Tiina_H
, Jul. 2022
Watching the sails go up and down was fun, especially since our daughter got to help. Beautiful views, nice crew. Great length of time. I liked that it was laid back; not a “party boat.”
icon Response from Host , Jul. 2022
Thank you for sharing your enjoyable charter with us aboard Tall Ship Windy, we love that your daughter helped us hoist the sails!
star-5
OUTSTANDING
Shenelle_T
, Jul. 2022
The crew was helpful , fun, and very engaging. Drinks for purchase were a great addition and the views were everything I imagined. Many beautiful memories and moments to take with me !!
icon Response from Host , Jul. 2022
We are happy you enjoyed all the aspects of our sailing charter! The Mermaid's Water is my favorite adult beverage! I hope you'll join us again soon!
star-5
Chicago sunset amazing
Darrell_B
, Jul. 2022
Enjoyed the boat ride of course. Because we used sails instead of motors it was quiet and peaceful. The staff were engaging and friendly, incorporated us to help with the sails, not mandatory but fun. Offered drinks and swag and some playful banter. The sunset was beautiful behind the Chicago skyline, would definitely do it again and encourage anyone us to join us next time. Ahoy !
icon Response from Host , Jul. 2022
Ahoy and thank you for the great review! We appreciate you enjoying the quietness with the sails; it is my favorite part of each sail. Join us again soon!
star-3
It’s okay if you like to watch sails hoisted
Michelle_B
, Jul. 2022
I would recommend this tour however I found it far too short. The ship sailed into the bay up to the light house which can be seen from shore. Shortly after departure it stopped in the middle of the bay to hoist sails. This took about 15 minutes. Afterwards, the ship bobbed for about half an hour allowing us to take pictures and ask staff questions . Then it dropped sails drove back to harbour. Had I known it wasn’t really a 75 minute tour on the lake I’m not sure I would have booked. I did enjoy it but by the time the ship got going after a cheesey pirate themed call of hoisting sales I really don’t feel I got the relaxation I was looking for. I care more about the sailboat experience and much less about watching sails get hoisted perhaps? A gentleman who was on board for his 50th (alone) sitting beside me was equally astonished that this really wasn’t a sailing trip at all but a hoisting sail demonstration/invite to participate- and promotion of their bar with just a few moments to fully enjoy the view and relax in the lake. I felt quite sorry for him as he wanted to enjoy the feel of the wind on a boat and the lake.
icon Response from Host , Jul. 2022
Thank you Michelle for your feedback. The majority of our guests enjoy our pirate calls, the bobbing (aka sailing) and the hoisting of our sails, as its such a unique aspect that most landlubbers do not get the opportunity to experience! We hope you'll give us another try and we will try to capture two more stars from you!
star-5
Great way to end a day
Tanya_M
, Jul. 2022
Great sailing tour. The sunset was stunning, the boat was clean and a smooth sailer. The crew was professional and made the cruise work for young and old alike. The view of the city is better then another. Highly recommend
icon Response from Host , Jul. 2022
Thank you for your lovely review, we appreciate you noticing the cleanliness of our ship. Our Crew work very hard to maintain her and we love that you took note! Please join us again soon!

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