The Bucket List Adventure You’ve Probably Never Heard Of

People dream of the Inca Trail. The Camino de Santiago. The Walk of the Gods in Amalfi.

All stunning. All challenging. All require stamina, planning, and a willingness to share your most unflattering angles in sweaty travel selfies.

But my bucket list adventure?

It’s not one you hike. You cruise it. Slowly, patiently, with one eye on the weather and the other on the depth finder.

Welcome to the Great Loop: a 10,000-kilometre waterway journey that’s equal parts logistics and magic.

This might not be Everest, but it’s no lazy river either.

So, What Is the Great Loop?

The Great Loop is a massive waterway route that circumnavigates the eastern portion of North America.

It winds its way:

Up the Intracoastal Waterway from Florida
Into Canada via the St. Lawrence
Through the Trent-Severn Waterway and Great Lakes
Then south again via the Illinois and Mississippi Rivers and other inland routes

Complete the loop, and you’re not just a boater. You’re officially a Looper.

And yes, there’s a flag. (It’s gold. It’s glorious. I want it.)

You get a gold burgee when you finish. It might just be a fancy word to say "flag", but this trophy-lover is sold!

Loopers Among Us

Every summer, the Kawarthas quietly becomes a stage for one of the biggest travel stories you’ve never heard.

Spend any time by the locks or local marinas, and you’ll spot them: sun-faded trawlers, sleek yachts, even the occasional houseboat—cruising through our lakes on their way across the continent.

Some of these boaters are retirees chasing a dream. Others are young couples remote-working from the water. I once followed the journey of a young man in a kayak completing the loop. People along the way fed him, offered bunkies, and cheered him on.

We live at the end of a bay—so the only time I see a big Looper boat is when someone takes a wrong turn. But I still go looking.

Thousands of people do sections of the Loop each year. A weekend here, a vacation stretch there. But only about 150 complete the full thing annually.

That’s fewer than summit Mount Everest most years—and Loopers do it with no Sherpas and far more pump-outs.

It’s Not for the Faint of Boat

This isn’t a pleasure cruise. It takes serious planning and nerves of steel (or at least, stainless steel cleats).

Loopers have to:

Know the specs of their boat inside and out—especially height and draft
Time their passage through the Trent-Severn, which shuts down in October
Navigate hurricanes in the south, freezing temps in the north, and the unpredictable moods of the Great Lakes
Plan around lock breakdowns—Kirkfield and Big Chute have both had issues in recent years

And then there's the cost: fuel, food, docking, maintenance, lockage fees. It adds up.

But so does the joy. Docktails with strangers. Sunrise crossings. Towns you’ve never heard of but will never forget.

Why It’s On My List

I live my summers vicariously through these adventurers.

There’s something romantic about a journey you can’t do quickly. One that requires patience, planning, and a bit of blind optimism.

We’re not on the official route here—our bay is a dead end for Loopers. But every now and then, one finds their way in by accident. And I drop everything to wave like I’m greeting royalty.

Because maybe one day, that’ll be me. Looping through the locks. Timing it just right. Earning my shiny flag.

It’s not about being the fastest or the strongest. It’s about showing up, staying the course, and making it through the locks before they close.

Want to Learn More?

If you’re curious about the Great Loop—or maybe thinking of trying a section yourself—you can find more information at the America’s Great Loop Cruisers’ Association.

Fast Facts About the Great Loop

Length: ~10,000 km
Time to Complete: 3–12 months
Annual Finishers: ~150
Official Recognition: Gold Burgee awarded by AGLCA

Thinking About Visiting the Kawarthas?

Whether you're boating, road-tripping, or just dreaming of slower days on the water—there’s something magical about summer in the Kawarthas. Get in touch if you'd like local insights or real estate guidance while you're here.

Let’s find your perfect place to anchor.