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Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner

Overview
The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday from Navy Pier. Leave the hustle and bustle behind, and enjoy a leisurely Educational Sail aboard Chicago’s Official Tall Ship.
Guests will enjoy 75 minute sail where they will learn about sailing and the history of Lake Michigan and Chicago. Ideal for youth groups, children, families and adults.. Chicago's history is forever linked to the history of sailing on Lake Michigan. From these historical maritime roots, guests will be delighted with interesting facts, unique stories, and a healthy dose of whimsy. You will have a chance to help sail Chicago's famous 148' Schooner and you will be rewarded with incredible scenery and photo opportunities of the Windy City.

Enjoy your time on the water — the third-largest of the Great Lakes, Lake Michigan is itself a natural wonder. Your guide will provide live audio commentary throughout the journey.

This is approximately a 75 Minute sail.
City: Chicago
Sat 19 Oct
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You can choose the date already on the booking website
Starting at $39.00
Sat 19 Oct
Starting at $39.00
Make a reservation
What's Included
Live audio commentary
Local taxes
Additional Info
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Children must be accompanied by an adult
  • Minimum drinking age is 21 years
  • Refunds will not be issued if tour/activity is missed due to late or non-arrival of cruise ship
What To Expect
1
Lake Michigan
Guests will enjoy 75 minute sail where they will learn about sailing, and some of the history of Lake Michigan and Chicago. Ideal for youth groups, children, families and adults.
2
Tall Ship Windy
Chicago's Official Tall Ship, Windy has been delighting audiences for the past 22 years. This educational sail is a highlight to any trip to the Windy City.
3
Navy Pier
Historic Navy Pier, one of Chicago's best attractions.
4
Chicago Skyline
Guests will enjoy 75 minute sail where they will learn about sailing, and some of the history of Lake Michigan and Chicago. Ideal for youth groups, children, families and adults.
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Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (46)
darlak2015
Jul 2022
I took my grandson on the windy tall sales tour. When I booked, I was told that it was not a pirate adventure. My grandson had been really disappointed because he loves pirates. So we were very pleasantly surprised that the educational tour definitely had the option on the main deck for pirate activities. My five-year-old grandson got to help lift the sales, pose with a pirate and had a fantastic time.
Response from Host
Jul 2022
We are thrilled to hear you and your grandson had a wonderful time! The educational charter is always exciting and full of pirate knowledge!
Kim_P
Jul 2022
We didn’t take the ride. It was pouring rain and the woman I talked to said there was no cover, and we were concerned because we were going to travel home in a car for 3 hours immediately following the tour. So that wouldn’t work for us. We paid $156 for four tickets which I’m looking at the pricing we paid a higher price for some reason, because we should have had a senior rate. We asked for a refund and we’re told no. So my review was not about the tour, it was about customer service.
Response from Host
Jul 2022
Kimberly Pillischafske, We regret you chose not to attend our excursion, we do sail rain or shine. I went through emails; you and I communicated and I did tell you we offered covering in the event of rain, and that we also have an interior Pub. We never discussed a Senior Rate, as we do not offer one. We trust this is simply an error on your part about the circumstances and hope you'll try us another time this season.
Sheila O
Jul 2022
It was nice overall, but it seemed like the crew could have done more. There wasn’t very much education or interaction. We didn’t travel very far- maybe that’s normal, or maybe it was because of a windy day. But since there was a fair amount of time with nothing really going on, it seems like they could have at least told us about some of the buildings that we kept looking at. The biggest negative was probably something they can’t control- and that’s the other guests. One of the few activities was to pull the ropes that raise the sails. Some 60 year old guy hogged one rope, and on the other rope in our area, my teenage boy grabbed it but was supposed to share with another girl about his age plus some random 30 something lady who wasn’t even associated with the girl. So my son bailed on the ropes
Response from Host
Jul 2022
Shelia Olson, thank you for your feedback on the Educational tour; we try to balance the educational aspects so as not to overwhelm guests with too much knowledge. Our Skyline excursion at 3:00 and 5:00 are the Architecture excursions where we discuss the buildings and the history of the city. We welcome all guests to participate in hoisting the sails, we regret that your son did not participate as he had hoped.

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