First steps in Siena: medieval charm and winding streets

I arrived in Siena just before noon today, the journey from Florence taking about an hour and fifteen minutes by bus. The ride itself was a treat - rolling Tuscan hills dotted with cypress trees and terracotta-roofed villas. I couldn't help counting the cypress trees until they became too numerous (127 before I gave up).

The bus station is located at the bottom of the hill, and Siena proper sits proudly atop. I've learned that Siena is built across three hills, which explains the constant up and down walking I've been doing since arrival. My calves are already feeling it!

Finding my bearings

After checking into my small hotel just outside the historic center (a charming place with creaky wooden floors and a tiny balcony overlooking a quiet street), I headed straight out. The medieval center of Siena is mostly pedestrianized, with narrow winding streets that seem designed to make you lose your sense of direction. And lose it I did, several times over.

I had scheduled a self-guided walking tour for 1:00 pm, giving myself exactly ten minutes buffer time to find the starting point at Porta Camollia, one of the city gates. Naturally, I was there at 12:50, which gave me time to study the ancient stone archway and snap a few photos before beginning my exploration.

The shell-shaped piazza

The absolute highlight so far has been Piazza del Campo, Siena's main square. Unlike the rectangular piazzas I've grown accustomed to in other Italian cities, this one is shaped like a shell or a fan, sloping downward toward the Palazzo Pubblico (town hall). I sat at a café on the edge of the piazza for about 30 minutes, just watching people cross the open space while sipping an espresso that cost twice what it should. The premium view tax, I suppose.

The Torre del Mangia tower rises impressively from the Palazzo, and I'm planning to climb it tomorrow morning when it opens. From what I've read, the 400+ steps offer panoramic views of the city and surrounding countryside that are worth the effort.

Contrade culture

One fascinating aspect of Siena I've started to notice is the contrade system - the 17 historic districts that divide the city. Each has its own symbol (eagle, dragon, she-wolf, etc.) and colors, proudly displayed on flags and plaques throughout their territories. It's not just a tourist curiosity; these districts compete fiercely in the famous Palio horse race twice each summer.

I wandered into what I later discovered was the Onda (Wave) contrada, identifiable by blue and white flags with a dolphin symbol. A small museum was open, and though I only had about 30 minutes before closing time, I got a glimpse into this unique social structure that has defined Siena for centuries. The elderly caretaker spoke little English but seemed pleased by my interest, pointing out photographs of past Palio victories with obvious pride.

Weather warnings and plans

The sky has been overcast all day, with the temperature hovering around 16°C - comfortable for exploring but not quite postcard-perfect for photos. I've noticed warnings about potential thunderstorms tomorrow evening and into the weekend. This might affect my loose plan to visit some surrounding villages, but I'll wait and see how the weather develops.

For now, I'm back at my hotel taking a short break before heading out again to find dinner. I've got my eye on a small trattoria recommended by the hotel owner, supposedly serving the best pici pasta in town. Pici is a thick, hand-rolled pasta typical of this region, and I'm eager to try the authentic version.

Reflections so far

Siena feels different from Florence - smaller, more intimate, and somehow more medieval in character. Florence has its Renaissance grandeur, but Siena feels like stepping further back in time. The streets are quieter, tourists fewer (though still present), and there's a neighborhood feeling that I didn't quite capture in Florence.

I'm glad I made the decision to come here rather than rushing off to Rome or another major city. After my experiences in Varenna taught me the value of slowing down, I'm trying to apply that lesson to how I experience Tuscany. Siena seems perfect for this approach - a place to wander without an agenda, discover hidden corners, and observe local life unfolding.

Tomorrow I plan to visit the Duomo (cathedral) first thing in the morning, then climb the Torre del Mangia. The afternoon might be dedicated to simply wandering and discovering, which seems like the best way to experience a labyrinthine medieval city like this one.

For now, my stomach is reminding me it's time for dinner. I've been counting the hours until I can try that pici pasta (exactly 2 hours and 17 minutes since I first read about it in my guidebook).

Day 80 of 500: 420 days remaining