Surprising Kayak Tours: Best Cities for Urban Kayaking

Paddle these urban waterways to get far from the maddening crowd

Chicago skyline dwarfs Chicago River. Photo taken near water level - urban kayaking Chicago
Chicago skyline dwarfs river. Photo by Antonio Gabola via Unsplash

Urban kayaking, the sport of paddling through urban city centers, might not be your first thought when considering outdoor adventure. However, once you put your kayak in the water at the bottom of a deep skyscraper canyon, you’re hooked. On these unexpected kayak tours, you’ll get a completely different perspective of the busy metropolis as you float peacefully along the water surface. Remove yourself from the maddening crowd that passes on bridges high above like cars on the Mouse Trap rollercoaster ride. You’ll feel as if you are in a world of your own, magically separated from all the hubbub. Grab your paddle and escape.

Urban Kayaking Chicago

Paddle “The Loop” through the deep architectural canyonlands of the Windy City as part of an architectural kayak tour. Put in on Magnolia Avenue to ‘get your Urban Kayaking on’ and learn about the city’s rich history, including Al Capone’s hideout.

Alternatively, do a lake paddle in a larger kayak out into Lake Michigan for views of the Chicago’s skyline. Urban Kayaking Chicago is one of the best urban kayak experiences out there. There are several kayak tours in Chicago from which to choose. Travel tip: be wary of larger boats while you’re paddling.

Kayaking Downtown Milwaukee, Wisconsin

Kayaker looks at Milwaukee skyscrapers while urban kayaking
UNSTOPPABLE Stacey photo.

Float by tall, turn-of-the-century Cream City brick buildings that create eerie deep canyons while glass skyscrapers loom above. Paddle to the Harley Davidson Museum. Explore the three rivers that bisect downtown metro area: the Milwaukee, Menomonee and the Kinnickinnic (fondly called the KK by locals).

UNSTOPPABLE Stacey paddles by Harley-Davidson Museum on one of the kayak tours in Milwaukee.
Kayak tours in Milwaukee take paddlers past the Harley-Davidson Museum.

Launch your own kayak or choose from a plethora of boat styles at Milwaukee Kayak Company. Located in a funky dry dock across the river from the historic Third Ward, Milwaukee Kayak Company outfits you for urban kayaking with almost any kind of non-motorized craft from kayak to SUP paddleboard to canoe.

Explore river corridors on your own or join a guided twilight paddle for your urban kayaking Milwaukee adventure. You’ll splash under swing, bascule and vertical lift bridges. A rusty swing railroad trestle from the old Northwestern Line lies downriver from the paddle shop, just before the river empties into the great Lake Michigan. For amazing kayak tours in Milwaukee visit www.milwaukeekayak.com.

Urban Kayaking Minneapolis, Minnesota

Kayaker on Mississippi River with Minneapolis Skyline in background during kayak tours in Minneapolis
Kayaker on Mississippi River with Minneapolis skyline in background.

Get into the water for an urban kayaking adventure through Mill City. Our guide offered history about how Minneapolis was built as a mill town at the location of the most significant drop of the Mississippi River. St. Anthony Falls attracted mill builders from the East who used the mighty waters to mill wheat, wool and lumber. Our adventure began at an office in the North Loop neighborhood where we first walked through the warehouse and former rail yard district for fun and informative history lessons.

Portaging kayaks through downtown Minneapolis.
Portaging our watercraft through downtown Minneapolis. It doesn’t get any more urban than that!

Afterwards, guides strapped wheels to the bottom of the kayaks, and we pulled our watercraft through downtown intersections and across boulevards. It doesn’t get any more urban than that!

We put in on the Mississippi River above St. Anthony Falls and had a choice of paddling north under Great Northern Railway bridges or south to historic Fort Snelling. I can’t recommend specific kayak tours in Minneapolis because the company that we went with is now out of business. So will have to ask your guide if you’ll see barges, beaver and the locks and dams as you glide through the Mississippi National River and Recreation Area while urban kayaking Minneapolis.

Kayaking Ottawa, Ontario

Rideau Canal with government building behind shows flat water for urban kayaking
Urban Kayaking Ottawa takes you past picturesque Canadian government buildings.

Dip your paddle into the Rideau Canal for a fascinating urban kayaking adventure. Float through the nation’s capital city on a flat-water system of waterways where water levels are controlled by 23 lockstations where you can put in or take out. You’ll float past the Canadian National Defense headquarters, Ottawa Convention Centre, National Arts Centre and Parliament Hill whilst urban kayaking Ottawa. Built between 1826 and 1832, the Rideau Canal is now a World Heritage Site. Check out the many rentals and kayak tours in Ottawa at www.rideau-info.com

Related Canal Story: 7 Reasons an Erie Canal Boat Trip Should be at the Top of Your Bucket List

Float past the Canadian National Defense headquarters, Ottawa Convention Centre, National Arts Centre and Parliament Hill whilst urban kayaking Ottawa.

Urban Kayaking New York City

New York skyline from the Hudson River
New York from the Hudson River. Photo by Peretz Partensky via Wikimedia

Paddle NYC waterways for free from several urban locations. Glide along the Hudson River, paddle under the Brooklyn Bridge or join a “Chill Sunset Paddle” for views of city skylines. The Downtown Boat House and Brooklyn Bridge Park Boathouse are two of the places where you can hook-up for the free kayak tours in New York City. Who knew, free urban kayaking New York City style?

Kayak inner harbor of Victoria, British Columbia

Victoria’s inner harbor at night fall reflects lights from the city
Find kayak tours in Victoria near the city's inner harbor. Photo by UNSTOPPABLE Stacey.

Kayak from Victoria’s inner harbor to explore back alley waterways of the city and local marine wildlife. Victoria Kayak Company, located near the famous Empress Hotel, guides you on historic and nature tours, or you may rent kayaks for your own self-guided urban kayaking Victoria adventures. Check out kayak tours in Victoria at www.victoriakayak.com

Urban kayaking is perfect for the solo traveler, couples, families or groups. Paddle urban waterways with a tour group, private group or in your own craft. It’s all good!

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UNSTOPPABLE Stacey originally wrote this article for Travel + Escape, the Canadian TV Travel Channel website. She updated links and information August 2019. The Arizona travel writer authored T+E’s “Adventure Travel” blogposts for over 18 months.

10 thoughts on “Surprising Kayak Tours: Best Cities for Urban Kayaking”

    • Thanks for you comment, Dena! I hope you can check out the new kayaking tours in Minneapolis before the snow flies!

  1. It had never occurred to me that I might Kayak the Hudson or East rivers in New York City until I saw this. I live in Connecticut, so this is an easy destination. What a great, healthy way to experience a place!

    • Right? And bonus: urban kayaking in New York City is offered for FREE in some places! Let me know if you check it out.

  2. Haven’t done this anywhere else, but Chicago is truly stupendous for this! The rivers, canals, and, of course, the Lake, all make for calm waters while enjoying the stunning city. I’ll have to keep the others in mind for some trips next year. Thanks!

    • Thanks, Rita. I so agree that Chicago is stupendous for urban kayaking! The amazing photo of the Chicago River is why I had to lead this article with urban kayaking in Chicago!

  3. I love urban kayaking!! I used to kayak all the time in Austin, TX. Here’s a tip: Instead of paying for tickets to the big music festivals, take your kayak out with a packed lunch and paddle out until you here some music playing then just coast. That’s how I could afford South by Southwest on a student budget! Plus, Austin is a great destination anyway!

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