The Great Loop: One Charted Course, a Thousand Wild Ideas

As a yacht broker, I get asked the same question at least once a week: “So, what’s the perfect boat for the Great Loop?” And while I’d love to deliver a straight answer, the truth is, there’s no single perfect boat. For me, it’s a 110-foot floating estate with a crew in matching polos, a butler in boat shoes, and a galley that would make a Michelin-star chef weep. But for someone else? It might be a 30-foot trawler. Or a 17-foot kayak. Or — get ready for this — a pair of Yamaha WaveRunners.

Yes, you read that correctly.

Have it your way

While the Great Loop may follow a charted course on paper, the experience is wildly individual. This month, I had the pleasure of speaking with Lakeland Boating editor Kate Bush about the intricacies of trailering Loop boats, but as our conversation wandered — as all good ones do — I realized this topic isn’t just about logistics. It’s about the astonishing, often hilarious, and totally unpredictable ways people tackle the adventure of a lifetime.

At a recent Looper event in Chattanooga, Tennessee, I met a couple in their early sixties who were positively glowing with excitement. As always, I led with my go-to: “Tell me about your boat!” Without missing a beat, she smiled and said, “Oh honey, we don’t have a boat. We’re doing the Loop on jet skis.” I stared at them, waiting for the punchline. There wasn’t one.

Now, I’m a lifelong Minnesotan, which means that for about half the year my primary mode of transportation is a snowmobile. I’ve racked up my fair share of miles hopping from tavern to tavern across frozen lakes, snow flying, face numb, heart full. So the idea of hopping on a jet ski and cruising the Loop? It’s not entirely outside the realm of possibility — it’s just an aquatic extension of a Minnesota winter pub crawl. I’ve also had those snowy moments when I stumble out of a warm restaurant and think, “Oh no, I have to ride that thing back home.”

Naturally, I couldn’t wait to call The Boss (that’s my wife, for the uninitiated) and tell her about this aquatic snowmobile stunt. Her reaction was instant: “Don’t get any ideas.” In fairness, she’s probably right.

But here’s the wild part—they had it all figured out. Spare fuel, route planning, overnight stops, even a makeshift cruise control system for her wrists. They were more organized than most yacht owners I know. And that’s when it hit me: the boat doesn’t matter. The dream does.

Paddle power

And speaking of dreamers, let’s talk about Peter Frank. This guy is doing the Great Loop in a kayak. Solo. No motor, no galley, no air conditioning, just pure grit and a paddle. I’ve been quietly (and obsessively) following his journey on Facebook, where every post is a heartwarming reminder of human kindness. People take him in, feed him, cheer him on. He’s become a living symbol of Loop spirit, and I love him for it.

This, my friends, is the magic of the Great Loop. It’s not about the bells and whistles. It’s about the boldness to go. And while some of us might dream of staterooms with marble countertops and built-in wine coolers, others are perfectly happy with a dry bag and a waterproof phone case.

The Great Loop is a canvas. Your mode of transport? That’s the brush. Whether you paint it in the sweeping strokes of a 50-foot trawler or the sharp dashes of a kayak paddle, the masterpiece is yours. Practicality doesn’t enter into it. And if you do decide to loop on a jet ski, bring a wetsuit.

(And maybe don’t tell my wife I’m pricing them out on Facebook Marketplace.)