The Best Cities for Urban Kayaking | Surprising Kayak Tours

UPDATED December 6, 2023–I was so surprised to get so much enjoyment from urban kayaking. I’m a small-town outdoors adventurer not particularly comfortable in major metros.

But I’m here to tell you that urban kayaking is a way to escape the maddening crowds quickly AND effortlessly. I think you’ll fall in love with kayaking tours in the city like I did!

In this article, you’ll experience kayak tours in

  • Chicago
  • Milwaukee
  • Minneapolis
  • Ottawa
  • NYC (New Your City?!)
  • Victoria, BC

So let’s get on with it! Dip, dip and swing ’em back!

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, you’re hooked once you put your kayak in the water at the bottom of a deep skyscraper canyon.

On these unexpected kayak tours, you’ll get a completely different perspective of the busy metropolis as you float peacefully along the water’s surface. Remove yourself from the maddening crowd that passes on bridges high above like cars on the Mouse Trap rollercoaster ride.

You’ll feel like you are in your own world, magically separated from all the hubbub. So 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.

Or kayak the Chicago River on Wednesday or Saturday nights to watch the Navy Pier fireworks display during the summer. You’ll have the best seats in the house!

If you or others in your party are not up for kayaking, take the Chicago Architectural River Cruise. I loved it!

Alternatively, do a lake paddle in a larger kayak out into Lake Michigan for views of Chicago’s skyline. Urban Kayaking Chicago is one of the best kayak tour experiences out there.

UNSTOPPABLE tip: be wary of larger boats while you’re paddling.

Book it now: urban kayaking Chicago.

RELATED: Chicago Architectural River Cruise

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 Milwaukee kayaking 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.

Book it now: kayak through Milwaukee

For unique kayak tours in Milwaukee, visit

Related: Milwaukee kayak rental

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!

Afterward, guides strapped wheels to the bottom of the kayaks, and we pulled our watercraft through downtown intersections and across boulevards. It doesn’t get 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.

We were fortunate to see barges, beavers, locks and dams as we glided through the Mississippi National River and Recreation Area.

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 Canada’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. It reminds me of my canaling adventures on the Erie Canal canal boat trip.

Book it now: boat cruise through Ottawa canals

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

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

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 free kayak tours in New York City.

Who knew, free urban kayaking New York City style?

Book it now: urban kayaking around NYC Statue of Liberty

Kayak Tours: Inner Harbor of Victoria, BC

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 the city’s back alley waterways 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 kayak adventures in Victoria.

We found some great kayak tours in Victoria BC at Viator. Or use your favorite online booking service.

And don’t miss the whale watching from Victoria BC, when you’re there! It’s some of the best on earth!

Book it now: urban kayaking through Victoria BC

Urban Kayaking Conclusion

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

RELATED: I Survived Kayaking the Hoover Dam

UNSTOPPABLE Stacey originally wrote this article for Travel + Escape, the Canadian TV Travel Channel website. She updated links and information in December 2023. The Arizona travel writer authored T+E’s “Adventure Travel” blog for over 18 months.

14 thoughts on “The Best Cities for Urban Kayaking | Surprising Kayak Tours”

    • 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!

  4. Kayaking the inner harbor at Victoria BC is a kick. But for the best (and safest) experience, it’s best to go with a guide. The bay is also the landing strip for sea planes….they come in and go out often. Plus, you’ll see a lot more with a guide…and get some good history.

  5. Hi Stacey,
    I would totally agree that there are many different types of kayaking, that are becoming mainstream, urban kayaking being one of them. Last year I went to vacation in Cocoa Beach, Florida and there I was introduced to a yet another type of kayaking that I hadn’t heard of before.
    The “Bioluminescence night tour kayaking”.

    The tour started around the beautiful sunset, as we explored mangroves around Thousand Islands. We also got to experience exotic wildlife first hand, like dolphins, manatees, herons and other kind of birds. As the sun went down we started to see bioluminescence in the water. They illuminated the water as we paddled and as our kayaks moved forward, forming a halo around our kayaks. We also saw comb jellyfishes that also illuminated at night.

    Over all it was a mesmerizing experience and I would recommend it to all of the aspiring kayakers to avail this experience if they are in Cocoa Beach, Florida.
    I’ll link the website of the kayak tour guide I had this amazing experience with, do check it out.
    Till then, Happy Kayaking 😀

    • Thank you so much for sharing your Bioluminescence kayak experience, David! This sound like just the kind of adventure experience that the UNSTOPPABLE community is seeking. Is the experience worth a trip to Florida? What would be the best way to make it a 3 or 4-day escape?


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