One Day, Three Skylines: Monteriggioni, Siena & San Gimignano

I didn't expect a tiny walled village to be the highlight of the morning. I was saving my excitement for Siena — the big name, the famous square, the whole reason I'd planned this route in the first place. Monteriggioni was supposed to be a quick photo stop.

It wasn't. And that's exactly why this day ended up surprising me more than once.

Monteriggioni: Small Walls, Big Opinions

You see Monteriggioni before you reach it — a perfect ring of stone with fourteen towers, sitting in the middle of the Sienese hills like someone dropped a crown in the grass. It's tiny. You can walk the whole thing in twenty minutes. But apparently it made enough of an impression back in the Middle Ages that Dante mentioned it in the Inferno, comparing its towers to giants. Not bad for a village you could lose in an afternoon.

I climbed up onto the walls — yes, you're actually allowed to walk along the top of them — and stood there for a while, half expecting a medieval guard to tell me to get down. Nobody did. Just me, the wind, and a view over the countryside that made the "quick stop" turn into forty-five minutes.

Siena: The City That Bets Everything on 90 Seconds

Nothing prepares you for Piazza del Campo the first time you walk into it. It's shaped like a shell, gently sloped toward the center, and it's somehow both grand and intimate at once. I sat on the warm brick for a while, eating gelato, and tried to imagine it twice a year packed with ten galloping horses during the Palio — a race that lasts less than two minutes but apparently means everything to the people here. Someone at a nearby café told me, half joking and half not, that locals think about their neighborhood's horse 365 days a year.

I climbed the Torre del Mangia after that — worth every one of the many, many stairs — and found out later that the tower is named after a notoriously gluttonous bell-ringer. Even Siena's landmarks have a sense of humor.

The Duomo was the real surprise, though. The marble floor inside is so intricate and valuable that for most of the year, it's kept covered. I got lucky and saw part of it uncovered — like walking into a museum that usually hides its own masterpiece.

San Gimignano: A Medieval Skyline That Still Competes

By the time I reached San Gimignano, the sun was lower and the towers were catching the light in a way that made the whole town look like it was posing for a photo. Fourteen towers still stand here, out of more than seventy that once existed — apparently the noble families of the 13th century were locked in a very literal game of one-upmanship, each building taller than the last just to prove a point.

I wandered the cobblestone streets without much of a plan, which is how I ended up at a gelato shop with a wall of awards behind the counter — actual world championship wins, not just marketing. I don't know if it lived up to the hype, but I finished the cone before I'd even decided.

What stuck with me most was learning that the local white wine, Vernaccia di San Gimignano, gets a mention in the Divine Comedy too. Apparently Dante had opinions about the wine here as strong as his opinions about the towers.

A Day of Small Surprises

I went in expecting Siena to be the main event, and it was — but Monteriggioni's quiet walls and San Gimignano's skyline ended up matching it beat for beat. That's the thing about stringing towns together like this: you never know which one is going to surprise you until you're standing in it.

Skip the Driving, Keep the Wine

Siena's one-way streets and San Gimignano's parking situation are not for the faint of heart. If you'd rather spend the day looking up at towers instead of looking for parking, our private transfer service takes care of the driving so you don't have to.

[Book Your Private Transfer →]

Curious about the rest of Tuscany? Read about Cortona, Montepulciano & Pienza · Pisa & Lucca · The Cinque Terre