San Gimignano is a small medieval hill town in the province of Siena, Tuscany, in central Italy. Sometimes called a "Medieval Manhattan", it's a remarkable town for its many tall stone towers, once defensive enclaves for the feuding town's families. Today it enjoys protected UNESCO World Heritage status and offers a glimpse into Tuscany's history, when the beauty of the landscape was also marked by small local wars and feuds over territory. The town was also once an important stopping post for pilgrims travelling to or from Rome on the Via Francigena.

Since its independence in 1199, the noble families who controlled the town built 72 towers, symbols of their wealth and power. Today, only 14 of the original towers have survived, maintaining the town's impressive skyline and providing enchanting views over the surrounding vineyards and olive groves. It is no wonder San Gimignano is so popular with visitors, providing the perfect example of medieval architecture, going on to influence the Florentine, Sienese and Pisa styles from the 12th to the 14th century.
What to see in San Gimignano
San Gimignano is not a large town and its centre is almost entirely pedestrianised so it is easily explored on foot.
Whichever side you arrive from, whether south or north, you will probably pass through one of the towns gates in the still extant circle of walls. If you arrive from the south you'll enter the town through Porta San Giovanni or Porta Senese. If you arrive from the north you'll enter through Porta San Matteo. Both gates are still impressive and look formidable. If you park in the Parcheggio di Bagnaia you will sneak through the walls of the city and onto Via Folgore.
Start by heading for the centre, for Piazza della Cisterna (which has a couple of excellent ice-cream parlours) and the neighbouring Piazza Duomo, dominated by the staircase leading up to the city's cathedral.

1. Basilica di Santa Maria Assunta
San Gimignano's duomo is unadorned on the outside and rather austere, belying the treasures that shelter inside. A church was first recorded on this site in 1056, and records show that it was dedicated to San Geminiano in 1148. Rather interestingly, around 1199, the whole church was turned around - a new facade was built where the apse once was. This reflects the rise in importance of the flow of pilgrims through the town, and the church was changed to now face the square and the road the pilgrims would take through the town.
In 1264 a local craftsman, Ranieri da Colle, was asked to build the staircase you now see leading up to the church. To do this he raided the nearby ruins of the village of Castelvecchio - you can visit this ruined village today, where the only building left standing is the church.
But it is the interior of this church that will take your breath away, almost completely covered with frescoes telling stories from the bible, like giant explanatory pages for the illiterate medieval church-goers.

The interior of the facade has the oldest frescoes, with work by Memmo di Filipuccio from 1305, the Universal Judgement by Taddeo di Bartolo, and in the centre a fabulous martyrdom of Saint Sebastian by Benozzo Gozzoli, from 1465.
To the left of the nave you'll see the frescoes of Bartolo di Fredi, painted in 1367, a cycle of Old Testament stories going from the creation of the world, Adam and Eve, Cain and Abel, Noah and the Ark, Joseph, Moses and the escape from Egypt, and the story of Jacob. Have fun trying to identify the stories and the protagonists, it's like reading a picture book, sadly with some 'pages' rather damaged.

To the right you'll find the New Testament, in a series of frescoes by two brothers, Filippo and Federico Memmi. Their work was influenced by the admiration of their brother-in-law, Simone Martini - you can see Simone Martini's work in Siena.
The panels go from the Annunciation, the 3 kings, the temple dispute, Jesus's baptism by John, the resurrection of Lazarus and on to the last supper, the crucifixion and finally, Resurrection.

There are many other worthwhile masterpieces in the interior of the church, I'll leave you to discover and admire them when you're there.
2. Climb Torre Grossa
You can't visit San Gimignano and not climb a tower, and the only tower open to the public is right next to the Cathedral, on the left when looking at the facade. Torre Grossa (big tower) is, as one would expect, the largest tower in the town. Fifty-four metres high, it is next to the Palazzo del Podesta. The climb is worth it for the fabulous views of the landscape, and the ticket you will need to see the Cathedral will also allow you access to the tower and to the Palazzo Comunale and the Pinacoteca

There were once 72 towers in San Gimignano, each associated with a powerful family within the town. The oldest is Torre Rognosa, still extant, which was built in the early thirteenth-century. By 1580 there were only 25 left standing as it was tradition to demand towers be shortened after a defeat in battle. Today there are about 15 - the precise number depends on how tall they still have to be to count as a tower. If you look at the buildings as you explore the town you can see the shortened remains of what were once proud towers.

Many other towns and villages had towers too, but few retained them past the sixteenth-century, and certainly none in the numbers that San Gimignano has. But you can often see the same shortened tower bases in other towns - for example there are at least that I've spotted in Casole d'Elsa.

Palazzo Comunale and Pinacoteca
The entrance to this is the same as that for Torre Grossa, so I haven't marked it on the town plan sketch. Once again, there are some amazing frescoes in here; San Gimignano is famous for its towers but the art is just as fabulous.

On the first floor you'll find the Sala del Consiglio also referred to as the Sala di Dante after the Florentine poet's visit to the city in 1299 as an ambassador for the Guelph League. The room is dominated by the magnificent Maestà painted in 1317 by Lippo Memmi. He was inspired by the Maestà that his brother-in-law Simone Martini painted for Siena, in the Sala del Mappamondo of Siena's own Town Hall in 1315.

If you climb up to the second floor (and why not, you're on your way to the ramps of stairs necessary to climb the Torre Grossa) you'll find the Pinacoteca. The art in the Pinacoteca goes from the thirteenth-century through to the fifteenth, with work from artists such Rinaldo, Taddeo di Bartolo, Benozzo Gozzoli and Pinturicchio. My favourite activity (and this works however much or however little you might know of the artists themselves) is to trace the increase in humanity through the paintings, going from the iconographic representations (where the figures faces are quite still and show little emotion, and the bodies are quite wooden) through to the fabulous work of the early renaissance where the figures seem to come life and show expression, movement and life.

3. Visit La Rocca and taste Vernaccia wine
To the west of Piazza del Duomo there is a fortress called "La Rocca di Montestaffoli", built on the highest point of the hill. Today it's interesting to walk around look out from the old city walls, imagining what it might have felt to be a medieval soldier on guard on a cold winter's morning, on the lookout for approaching enemy troops. The Rocca also houses the Vernaccia Wine centre which you can visit to learn more about San Gimignano's white wine, and have a tasting experience too.
4. Chiesa di Sant'Agostino
At the northern end of the town you'll find the Chiesa di Sant'Agostino, like the Duomo, an austere building from the outside, but with some beautiful artworks on the inside. Most notable are the cycle of frescoes telling the life-story of Sant'Agostino, painted by Benozzo Gozzoli in 1464, and, by the same artist, a fresco of Saint Sebastian and his followers. This is a very unusual piece as Saint Sebastian is always shown naked and tied to a post during his martyrdom pierced by arrows but Benozzo Gozzoli shows him instead clothed and offering shelter to the population from the arrows of misfortune that God, in his anger, is firing down at the people of San Gimignano.
There is also a piece that has added historical interest, a fresco by Bartolo di Fredi with scenes from the life of the Virgin. He painted this in 1374, copying works that Simone Martini and the two Lorenzetti brothers had frescoed onto the facade of Santa Maria della Scala in Siena.
5. Ornithological Museum
A rather random museum, born of a donation made to the city in 1927 by the extravagantly named Marquise Marianna Panciatichi Ximenes d'Aragona Paolucci of his collection of stuffed birds. Today it's housed in the church of San Francesco, in via di Quercecchia. Opening times are varied, random and sporadic, so this is a pot-luck mission - you may end up looking at a locked door.
6. Medieval Water Fountains
On the east of the town one of the fortified town gates leads out to medieval public fountains, where once the local people drew water, and washed their cloths. The stone arches of the fourteenth-century fountains conceal the first Lombard stony fountain dating back to the ninth century. The "Porta delle Fonti" was part of the second circle of walls, but was sadly altered during the twentieth century. The chapel built on the gate in 1501 was demolished, and the fresco of Virgin with child, St. Michael, and St John the Baptist. was transferred from within to a position under the lodge of the Town Hall.

7. San Lorenzo al Ponte
The Church of San Lorenzo al Ponte is one of the oldest in San Gimignano, named "al Ponte" (by the bridge) because it was close to an old drawbridge from the Castle of the Bishop of Volterra onto the street that leads up to Piazza della Cisterna. Today the Bishop's old castle is an ex-prison, the small thirteenth-century church is still next to it, but the drawbridge is long gone.
This Romanesque-style church is simple, with a single nave beneath a roof with wooden trusses and a raised, vaulted chancel. Under a small portico Simone Martini once painted a Madonna and child. The bodies of the Virgin and of baby Jesus, along with the corona of angels in glory, were renovated in the 1400s, but the face of the Madonna herself is still the original work of Simone Martini, the ultimate exponent of Sienese Gothic art, early on in his career.
Devotion to this early work by Simone Martini led to an expansion of the original portico which was then decorated with a cycle of frescoes on the theme of the afterlife, painted by Cenno di Francesco di ser Cenni. The patron saint of the church, San Lorenzo, was granted the ability to save souls from purgatory, hence the cycle with evocative details of Hell, Purgatory and Paradise. At some point the portico was walled in to protect the paintings and today you can visit it as a museum.
Parking in San Gimignano
There are three main places to park in San Gimignano but, be aware that the town can get very busy in high season and it can be tricky to find a parking spot.
P1. On the approach to the town from the south. Google Maps to P1 San Gimignano
P2. Parcheggio Montemaggio, close to the Porta Senese. Very handy but often busy. Google Maps to P2 San Gimignano
P3. Parcheggio Bagnaia. To the north of San Gimignano - has the longest walk in but is my favourite as it's quieter. Google Maps to P3 San Gimignano
Where to stay near San Gimignano
We have a number of villas in the area, the closest is undoubtedly Casa Andrea, a lovely house with a hot-tub just 4km from the town. You could even walk in if you're happy walking.

Wine Tasting around San Gimignano
If you'd like to round off you day with some wine-tasting in the wineries around San Gimignano, here are some addresses for you:
Azienda Agricola Palagetto Via Racciano, 10, 53037 San Gimignano
This long-standing local winery offer a variety of wine-tasting packages, from a simple tasting to a lunch. They all must be booked in advance, so we've added some links:
Palagetto 1 hour wine tasting from €25 per person.
4 wines and a selection of cold-cuts and cheeses to accompany
Palagetto light lunch and wine tasting, from €37 per person
The experience includes the tasting of four Palagetto wines accompanied by a rich Tuscan light lunch, including a platter with typical Tuscan cold cuts like salami, ham, finocchiona, a selection of Tuscan pecorino and mixed bruschetta; followed by a Tuscan first course. To conclude on a sweet note, you'll enjoy cantucci cookies accompanied by Vinsanto.
Azienda Agricola San Quirico Località Pancole, 35, 53037 San Gimignano
Gourmet Wine Tasting and Tour, from €25 per person
A tour of the Cellars and explanation of the main winemaking techniques, followed by a guided wine tasting. The tasting will be accompanied by a small selection of local cold cuts, cheeses, and bruschetta with organic extra virgin olive oil from the fattoria itself.

FAQs about Exploring San Gimignano
1. How long do you need to see San Gimignano?
The town is quite small, you can easily visit it in half a day, but there is plenty to see if you wish to dig a little deeper, and lots of places to visit in the surrounding area, so we'd include San Gimignano in a list of towns that make a long holiday in the area worthwhile.
2. Can you walk on the walls of San Gimignano?
San Gimignano still has most of its walls and you can walk most of the 2km+ perimeter. The path along the walls above the medieval founts has beautiful views, as does the section along La Rocca, to the west of the Cathedral
3. What day is the market in San Gimignano?
San Gimignano has a wonderful fruit and vegetable market held every Thursday in the three main and conjoined squares: Piazza della Cisterna, Piazza Duomo and Piazza delle Erbe. From 8 a.m. to 1.30 p.m. you can explore this extensive marketplace with fruit, vegetables and cheeses for sale, as well as handicrafts and local food and wine products.

Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
10th Dec 2024 10th Dec 2024