Discover the timeless charm of Tuscany’s medieval hilltop town
There’s a town not far from Florence, somewhere between the rolling hills on the way to Livorno, where time doesn’t rush. In San Gimignano, the Middle Ages aren’t just history—they’re carved into the stone walls, echoing through the narrow streets and rising in the watchful towers.
I return here often. Our road trips through Tuscany seem to always pass through this place. Maybe it’s because it feels good to know that some towns still resist the pull of modern life. In San Gimignano, memory leads the way—not progress.
As we approach, the famous skyline emerges—those tall medieval towers reaching above the green hills like ancient sentinels. They call it the “Medieval Manhattan,” and they’re not wrong. Once home to more than 70 tower houses, 13 remain today, each one a silent witness to centuries of rivalry, pride, and artistry.
I love San Gimignano.
There’s a quietness in the stones that’s hard to explain—like the past and present are holding hands. The alleyways cast deep shadows, the towers stretch skyward, and the sun brushes golden tones onto every facade. I sit on the stone edge of Piazza della Cisterna with a macchiato in hand, watching life unfold: pigeons fluttering, locals strolling, the gentle heartbeat of a lazy afternoon.
But don’t just come for the towers. Step into Galleria Continua—a contemporary art gallery housed in an old cinema, with another space overlooking the main square. It’s one of Italy’s most surprising cultural gems, yet still under the radar. Like the town itself, it manages to be both ancient and quietly modern—never loud, but deeply present.
And then… the gelato. No Italian town visit is complete without it. You’ll find Gelateria Dondoli right on Piazza della Cisterna. It’s hard to miss—there’s always a line, even in the colder months. Frequently named among the best gelaterias in the world, it offers flavors you won’t find anywhere else: dark chocolate with chili, or even white wine sorbet. Strange? Maybe. But they work. My favorite ritual is to grab a cone, find a spot on the warm stones, and just sit there in the shadow of the towers, sharing the moment with locals and sun.
San Gimignano isn’t just a destination—it’s a feeling. The echo of footsteps on cobblestones, the afternoon light slanting across archways, the silence behind medieval gates—all seem to whisper: “Don’t rush. Stay a little longer.”
This town doesn’t race, doesn’t strive to be more than it is. And that’s exactly what makes it so unforgettable.