Breadcrumb Adventures

By Joe B., Co-Founder of The Joes

There’s a certain magic in not knowing exactly what’s next. We call it following the breadcrumbs, those tiny clues that nudge you toward something unexpected: the narrow staircase behind a café, the unmarked path cutting through a park, the whispered recommendation from a bartender who clearly likes you. Credit where it’s due: Joe R., our rational, steady-handed CEO, coined the phrase. He has a knack for pulling the perfect words out of nowhere. In our many conversations about travel, he framed breadcrumbs as that half-clue, half-invitation that points you somewhere new without giving away the ending. It’s the road less taken, and nine times out of ten, it’s the one that delivers the biggest return.

I’ve always been pulled toward the unknown. Years ago in Venice, I once wandered down a tiny alley chasing the sound of a fountain. At the end, I stumbled upon a little shop filled with hand-painted papier-mâché masks, a locals only kind of place. I bought a beautiful moon mask for 10 euros and it’s still hanging in my home today reminding me of that wonderful discovery. None of it was on the tourist map, and that’s exactly why it mattered.

Years later, in the tiny country of Andorra, my son and I set out on a simple walk. We could see a trail etched into the mountainside, and curiosity pushed us to hunt for it. After searching, we finally found the path and climbed upward, eager to see where it would lead. At the top, we found ourselves looking out at the whole country in one breathtaking sweep. That moment is etched in me, not because it was planned, but because it wasn’t. These are the breadcrumbs that shaped how I travel and, in many ways, how we built The Joes. I’ve learned that the best stories don’t come from itineraries. They come from curiosity, detours, and serendipity.

The same spirit lives right here in Wine Country. If you want to follow your own trail of breadcrumbs, there are plenty of places to start. A few of my favorites… at Riverfront Regional Park there’s a sandy beach that’s perfect for launching into the Russian River. Of course, the trail isn’t marked and it feels like trespassing to get there. Thanks to seasonal dams, the river turns calm and easy, ideal for paddle-boarding without breaking a sweat. It feels like summer’s secret hack.

In Jenner, River’s End is an iconic spot for a cocktail, perched above the Pacific where the river meets the ocean. For me, the breadcrumb is personal: Burt Rangel, a friend and host who embodies hospitality. Go for the view, stay for Burt, leave knowing you’ve touched the edge of something timeless.

In San Francisco, breadcrumbs hide in plain sight: tiled steps, quirky slides, micro-parks tucked into steep hillsides. Every neighborhood holds a little gem if you let yourself wander.

And here’s the beauty of staying for 30 days or more, you actually give yourself permission to get off the beaten path. When you’re somewhere for just a few days, every moment feels high-stakes, and you can’t afford a misstep. But when you’ve got a whole month, you can chase breadcrumbs without pressure. Some adventures will be spectacular, others less fruitful, but it doesn’t matter, you’ve got the time to try, to explore, to double back and discover again. That’s when the real magic happens.

So how do you travel with breadcrumbs? Pick one destination and give yourself permission to drift. Take a tip from a local, then ask the next person for something different. Notice the textures - alleys, stairs, waterfronts, rooftops. Anything unusual deserves a detour. And most importantly, forget efficiency. The best stories never start with “I optimized my route.”

The Joes was built for travelers who crave more than a landing pad. Our homes sit in places with stories hidden around every corner, destinations where a month gives you space to wander, to chase breadcrumbs, and to return with tales you couldn’t have planned. And if you ever need a starting clue, we actually include breadcrumb recommendations at every home, they’re enough to get you moving, while leaving plenty more waiting to be discovered so the wonder never gets spoiled.

P.S. Full credit to Joe R. for coining “breadcrumbs.” He names the compass, I chase where it points.