One Day in Siena | The Jewel of Tuscany

I’ve only ever visited Siena spontaneously.

The first time, I was a college student studying abroad. During a few days in Florence, my friends and I decided to take a day trip to somewhere else in Tuscany. Since this was 2008 — before any of us had smartphones, and before the web filled up with travel blogs — we picked Siena sort of at random.

It was a glorious day: we discovered one of Europe’s best piazzas, had a blast at a soccer game (okay, okay: football game) we bought tickets to for reasons I can’t recall, and ate some excellent pizza. I’ll never forget the thrill of riding through the Tuscan countryside in the front of a double-decker bus with friends on the way to a city we knew nothing about to do who knows what — and then totally loving what we found there.

During my next trip to Italy — a full month in 2023 — I didn’t plan to return to Siena. Instead, I intended to rent a car, pick up a friend from Rome’s airport, and drive together to Civita di Bagnoregio — a tiny town that can’t really be reached by train. We would spend one night there before driving through Tuscany to San Gimignano.

But, in one of my more egregious travel mistakes, I forgot to take my driver’s license to Italy, and the car rental company — understandably — would not give me a car. We were stuck, and had to pivot quickly. Where, between Rome and San Gimignano, could we travel by train ASAP? It needed to be somewhere that would be easy to reach, since we had just 24 hours or so before we would move on to San Gimignano and didn’t want to waste a ton of time on traveling — and ideally it would be somewhere interesting enough to soothe the sting of missing out on Civita di Bagnoregio.

Well, the answer seemed obvious: Siena.

In a hurry, we booked the next train from Rome, plus lodging for that night, and zoomed off to Siena.

What we found there: a town in celebration mode (victory parade and all) after the recent horse race, a cathedral with a truly jaw-dropping interior, spectacular views of Tuscany, and — once again — one of Europe’s most astonishing piazzas. (Seriously. It’s a great piazza.) Not only did Siena make me feel okay about missing Civita di Bagnoregio, but I left Siena delighted that we had been forced to change our plans.

Indeed, visiting Siena again, after 15 years, affirmed that it’s a truly special place — and that it wasn’t just the stars in my 19-year-old eyes the first time around. Now, it’s one of my favorite places in Italy.

Here’s how we spent one day in Siena.

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Arriving in town

We arrived in Siena in some godawful August afternoon heat. The Siena train station is a bit outside of the historic town center, so we rode about 74 escalators (okay: maybe, like, 4) to a bus stop above the train station and hopped on a bus to our hotel.

We checked in at our last-minute lodging — Tetti di Siena — cleaned ourselves up, and headed toward Piazza del Campo, Siena’s famous main square.

As we walked, we noticed small groups of young men installing colorful lighting and flags along the city’s streets. We didn’t think much of it at the time, but — spoiler alert — we would soon find more meaning in it.

I liked Siena immediately. The warm stone buildings glowed in the late afternoon sun, and the hilly streets were full of life.

An unexpected victory parade in Piazza del Campo

We soon arrived at Piazza del Campo — a remarkable, vast plaza.

Piazza del Campo is shaped more or less like a trapezoid. The three shorter sides are lined with cafes and restaurants under red awnings, while the longest side of the square is largely filled with the Palazzo Pubblico — Siena’s historic town hall — and dominated by the massive Torre del Mangia. This tower is nearly 300 feet high, standing tall over the square and all of Siena.

And the whole square is unmistakably, dramatically sloped — all pouring down a hill to the tower.

We knew we didn’t want to eat dinner at the piazza, since food at major tourist spots like that one is often overpriced and subpar, but we did want to hang out there for a bit, so we grabbed an exterior table and ordered a few glasses of wine.

As we sat facing the tower, soaking in the energy of the piazza, we soon noticed a large group of people gathering in one of the corners of the square — and starting to parade around it.

We had little idea what was going on, but we had one guess: didn’t the Piazza del Campo host an annual horse race? What if the race was, magically, the next day, and this was an introductory event of some kind?

Well, no. As it turned out, the infamous Siena horse race had occurred just a few days before our arrival. But this parade WAS about the horse race. (FYI: the race is called the Palio di Siena, and it actually occurs twice per year!)

Backing up for a second, it’s important to understand that Siena is divided into 17 contrade, or districts, and that these contrade are a huge part of Sienese identity. There are rivalries,

So, at the race that we just missed, the Contrada dell’Oca — the District of the Goose — won the Palio for the first time in 10 years. We had accidentally stumbled into their victory parade! And it was substantial, with hundreds of people passing by, many waving flags and some pounding drums. Nearly all of them were wearing a green, red, and white scarf with the symbol of the contrada. (Yes: the same symbol on the flags the young men had been installing in the streets earlier.)

They did a full lap around the piazza and ultimately gathered at the bottom of the hill, near the tower. We watched their joyful celebrations as we sipped our wine.

Eating perfect pici

Eventually, we left the piazza to seek out food. We settled on a tiny restaurant on a quieter street, and ordered pici — a signature pasta of Siena. Think: thicker, doughier spaghetti. As an avowed lover of dough, I find it delicious.

After dinner, we opted to walk around a bit before returning to our hotel. In the process, we stumbled upon even more of Oca’s celebratory party, finding a street full of Oca flags and happy revelers.

Admiring the Torre del Mangia

The next morning, after eating breakfast at our hotel, we returned to the Piazza del Campo to get another look at the Torre del Mangia.

Given the heat, we opted not to climb the tower, but we did walk into the open-air courtyard of the Palazzo Pubblico to get a cool glimpse of the tower above us.

Stunned by the Siena Cathedral

Then, we headed over to the Siena Cathedral. We hadn’t bought tickets in advance, of course (since we didn’t plan to come to Siena at all!), so we waited in line for tickets to enter the cathedral.

The Siena Cathedral tickets include entrance to a lot of different parts of the cathedral complex, although some of them were already fully booked up for the day. No matter: we got to experience the most important one, which is experiencing the inside of the cathedral.

It is unusual and spectacular, with soaring arches, intricate floor mosaics, and — most memorably — walls and pillars constructed in stripes of white and black. It’s a visual feast.

Our tickets to the cathedral complex included a self-guided audio tour (accessed through a smartphone app), so we took our time exploring the space and listening to the information provided on the tour.

Views from the Facciatone

When we were done with the interior cathedral, we headed over to the Opera delle Metropolitana — a museum to the side of the cathedral complex. Admission was included in our cathedral tickets, although in all honesty, we were not too interested in the museum itself.

Instead, our purpose for going to the museum was to see the views from the Facciatone — a viewing platform that you enter via the museum.

We had to wait in line for a little while, but eventually we were able to access the platform.

Entry to the viewing platform (which is actually two different levels) is highly choreographed, with visitors permitted to stay in each area for just a few minutes at a time and then firmly ushered onto the next section.

Nonetheless, it was worth waiting in line — those views! We could see the cathedral right across from us, a sea of rooftops below us, Piazza del Campo and Torre del Mangia just a few blocks away, and the Tuscan countryside in the distance. Absolutely beautiful.

Lunch in a Cave

After leaving the cathedral complex, we wandered around in search of a good lunch — and found it in a small restaurant inside a cave-like setting. This was a welcome relief from the hot, hot, crazy hot (did I mention hot?) August weather in Tuscany.

Saying arrivederci to Siena

Alas, our time in Siena had come to an end, and we took one final walk through town before heading to the bus stop and moving on to San Gimignano.

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