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Chuck's Chicago Adventure: Sailing and paddling around the 'Windy City'

While taking a kayak or tall ship might be an unusual way to get around Chicago, they certainly are peaceful.


For the latest Chuck's Big Adventure, we traveled to Chicago for a trip that took us to Wrigley Field, showed us super heroes, had us tasting the best pizza, and touring the city by water.

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Urban Kayaks

Peace in the middle of a major world city? I would have thought that would only be possible in a chapel, stretching class or a hot tub. To my surprise though, I found peace paddling down the Chicago River in the midst of skyscrapers, and I will never forget the experience. Urban Kayaks has slowly built a real presence on the Chicago River, near Wacker Drive, over the past eight years. COVID-19 shut them down of course, but since they have reopened, business is booming. Paddlers join a tour guide and head west on the river, with the guide giving a historic glimpse at the buildings as well as answering questions. 

Credit: WTHR
Urban Kayaks has slowly built a real presence on the Chicago River near Wacker Drive over the past eight years.

It's a fascinating trip with one-of-a-kind looks at buildings on a body of water that has become much cleaner in recent years. Asher Gershenzon owns Urban Kayaks. 

"Well, you know, we started off, and we were given year-to-year contracts. I guess the city wasn't so sure people wanted to kayak the Chicago River," Gershenzon said. "And over the years, we've just noticed that drastic change of the Riverwalk, along with the river in the water quality on the river, has improved greatly over the years, and it was a big – Rahm Emanuel was a big promoter of cleaning up the river, and he did a great job. And, you know, more and more kayaks are coming every year.” 

Paddling down the river, we learned about the architectural secrets of Trump Tower, the gangster inspired history of the Jewelers Building and how the Chicago Fire impacted Chicago – even to this day. 

Credit: WTHR

My paddling partner Quentin and I, along with our crew, were out on the river a couple of hours and I felt it the next day. But wow, what an experience. 

"You know there are not many cities that you could kayak through downtown of the city, and there's kind of a canyon of buildings on either side while you're kayaking through, and it's a beautiful view of Chicago," Gershenzon said. "We also have a lakefront location a few blocks away where you kayak on Monroe Harbor, and that one's a little more calm if you're afraid to kayak on the river. So, we have both options for the calm kayak paddler, and then also going on the main branch of the river for the more active type." 

Both excursions are memorable and yes, even peaceful. You aren't fighting traffic, bumping into people or hailing a cab. You are simply enjoying the beauty of a great city...one paddle at a time. 

Tall Ship Windy 

Credit: WTHR
The Windy is moored near Navy Pier and was specially designed to take passengers out on the lake more than 25 years ago.

The Big Adventure series has taken my team and me on a ferry racing across the Straits of Mackinac, riding a four-wheeler on an ice-covered Sturgeon Bay and jumping dunes in a Jeep in Western Michigan. The trip to Chicago brought with it a wonderful trip on beautiful Lake Michigan on our most unusual mode of transportation yet: a tall ship. 

The Windy is moored near Navy Pier and was specially designed to take passengers out on the lake more than 25 years ago, according to Captain Rod Randall. 

"This is the premier sailing ship for the city of Chicago. This is the one and only place you can actually get out on a four-masted schooner and actually set sail and go sailing in the city," Randall said. "It was built in 1995, and it was purposely built to come here, when they were rebuilding Navy Pier to make it a tourist event, and this was built to be purpose-driven to be a tourist attraction to take people sailing and expose them to sailing events on the water.”  

The vessel holds 150 people at one time and has the capability to house people overnight. The captain, along with a six-person crew, actually live aboard the ship right now.  

Captain Rod's brother, Bruce, and his wife, Karen, brought the boat to Chicago and still own and operate it. They want passengers to enjoy a slow, steady view of the city and to learn what seamanship looks like up close. 

I joined a few other passengers in lifting the heavy masts and setting the sails. It was a thrill, and as the wind picked up, it was easy to see the difficulty and the beauty of setting out on a maritime journey. 

This is a great trip for kids and families, as well as couples wanting a romantic and unique trip. The Windy is a popular vessel in the evenings as it sets out in the lake and gives passengers a beautiful view of the Navy Pier fireworks. I LOVED this trip and can't wait to have family and friends give it a try. 

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