San Gimignano, the medieval Manhattan of Tuscany

San Gimignano in Tuscany is a medieval hilltop town and is popular with tourists all year round. Tourists come to visit the Duomo, climb the famous towers and enjoy seasonal locally produced food, not to mention the gelato. San Gimignano is instantly recognisable from its fourteen medieval towers that can be seen for miles. I first visited San Gimignano in 1999 and had planned to spend a few nights there. I ended up staying for eight. It proved a great place to stay and relax in. Also, a perfect base for the surrounding towns and daily hikes through the vineyards. Here are my memories of San Gimignano.

First Impressions

I still remember clearly planning my first trip to Italy way back in 1999. I would be spending 3 weeks in Tuscany. San Gimignano did feature, but as a two or three-night stop en-route to Siena. When I finally arrived in San Gimignano after four nights in Florence, I must admit I wasn’t that impressed.

I arrived mid-afternoon by bus and entered one of the city gates and found myself immediately walking against crowds of people coming towards me. Every conceivable space was filled with people. I was staying at the youth hostel, which was at the other end of the town.

Changing Impressions

After checking into the youth hostel (since closed), I braved the crowds once more. I followed some signs up to the Rocca to view the city. I was immediately transfixed, and I could now see why people come to San Gimignano. San Gimignano is a beautiful town.

Viewing the town from the Rocca, up high, I could see the impressive medieval towers up close, as well as, the stunning terracotta roofs all set against the Tuscan countryside. My impression of San Gimignano was changing. This was confirmed when I returned to the main street, and I noticed the crowds had all but disappeared. I kidded myself, I was now a local.

Why so many towers?

Today fourteen towers remain, but go back 650 years, and there were around 70 towers. For many years San Gimignano was under the control of the diocese of Volterra. In 1199, they declared independence from them. This did not stop San Gimignano from being dragged into the conflicts of the two feuding city-states, Florence and Siena.

As a consequence, wealthy families of the town began to build tower houses. This resulted in competing families building towers at increasingly higher heights. By the fourteenth century, there were 72 towers, with some up to 70 metres tall. Eventually, the town council of San Gimignano declared that no towers could be taller than the Palazzo Comunale.

San Gimignano continued to grow until the Black Death in 1348. Weakened by the plague, the town surrendered to Florence, and a new style of architecture appeared, Gothic in the Florentine form. Many families restyled their palazzi and reduced them in size, including the towers. Consequently, today, around 14 of the medieval towers remain.

Exploring San Gimignano

If arriving by the hourly bus from Poggibonsi (nearest railway station), you’ll be dropped off at the carpark by Porta San Giovanni.

Here the street, Via San Giovanni begins, gently uphill to Piazza della Cisterna. Along the way are several shops selling local foods, wine, handcrafted souvenirs and clothing, as well as cafes, restaurants and wine stores (enoteca).

There are also many stairways and alleyways to distract you. I found one that allowed me to reach Piazza della Cisterna at a more relaxed pace.

Piazza della Cisterna

Piazza della Cisterna is a triangular-shaped piazza. It is also home to the world-famous Gelateria Dondoli.

At the centre of the piazza is a medieval well. I have many great memories of sitting by the well relaxing in the late afternoon sun after a day of sightseeing. Then, in the evening, eating a pizza.

Piazza Duomo

Continuing from this piazza is Piazza Duomo, home to the Duomo, the Collegiate Church and two palazzi, Comunale and Podesta. The latter is the largest of the two with a large shady loggia. It’s also a great place to people watch, enjoy the cool shade while enjoying a gelato!

Moving beyond Piazza Duomo, the narrow main street is uphill and downhill with similar shops. I found this part of the town more relaxing. The crowds tend to drop off in Piazza Duomo. I tried some lovely Vernaccia (locally produced white wine) at an enoteca.

Piazza Sant’Agostino

The Chiesa di Sant’Agostino in Piazza Sant’Agostino is a must-see.

Built-in the thirteenth century, the inside is a large hall with a 17-panel fresco depicting the life of St Augustine by Benozzo Gozzoli.

The Rocca

Other places recommended to visit are the Rocca. A climb up the narrow stone stairway affords you stunning views of the town with its towers.

Immediately beyond the town is the Tuscan countryside. The hills are dotted with wine-producing vines.

Walking the hills around San Gimignano

It is possible to walk part of the pilgrimage trail, the Via Francigena. San Gimignano is a major stop on this trail.

It is but a short 1.5km walk to pick up the path. The excellent tourist information office in San Gimignano has maps of the area that show the walking trails.

In and Around San Gimignano

In 1999 I used San Gimignano as a base to visit Monteriggioni, Siena, Colle Val D’Elsa and Volterra. I visited these towns by bus via Poggibonsi or Colle Val D’Elsa.

San Gimignano is surrounded by beautiful countryside, much of which is made up of vineyards and farms. It is possible to visit San Gimignano from either Siena or Florence in a day.

Revisiting San Gimignano

After spending eight nights in the town in 1999, I have since returned three times. Most recently, I visited in 2018, and enough time had elapsed for me to enjoy the town all over again. I had a great day exploring San Gimignano. I was walking up and down the tiny streets, walking up to the park where the Rocca is.

Interestingly, I revisited many of the churches I had first seen nearly 20 years ago, but now with better-informed eyes. Now I have a better understanding of Renaissance art (and earlier). One thing that hasn’t changed though is the popularity of the gelati store in Piazza della Cisterna.

The queue these days stretches way beyond the shop front. In fact, it now extends far beyond the well in the centre of the piazza. Sadly, our favoured pizzeria in Piazza della Cisterna is no longer there. I also have a greater appreciation of the locally produced Chianti and Vernaccia wines too!

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