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San Gimignano

A Medieval Manhattan of Gothic stone towers and frescoed chapels from the early Renaissance, plus Tuscany’s noblest white wine

By: Donald Strachan Writer & Journalist | Specialist in Italy & European travel

San Gimignano travel guide

Guarded by a ring of fortified walls, Tuscany’s “Medieval Manhattan” is a small town of gnarled stone palaces and narrow, winding lanes. Its preserved Gothic centre is a magnet for visitors, certainly, but in its backstreets and frescoed churches, you can still find a corner to yourself.

Twenty-five miles north-west of Siena, this is one of Italy’s most spectacular hill-towns, known for its surviving medieval towers, the frescoed interior of its Collegiata, and the fine white wine made from grapes picked on the surrounding hills: Vernaccia di San Gimignano.

If you can fit it into your itinerary, try to visit San Gimignano early in the morning and at dusk. Without the day-trippers, the place takes on an entirely different atmosphere: secretive, silent, even a little spooky. Standing alone, in Piazza della Cisterna, the town suddenly feels every one of its eight hundred or so years of age.

In the Beginning...

The towers and stone streets have hardly changed since the Middle Ages: San Gimignano is a tiny town where time seems to have stood still. At least, that is how it looks — its medieval street-plan is almost entirely unaltered, and Gothic palaces that once housed squabbling noble families are still standing with hardly a brick out of place.

The town’s most famous feature — which earned it the nickname “San Gimignano delle belle torri” — are its towers. Only 13 remain, from a total of over 70 at the peak of its wealth and influence in the 1300s.

San Gimignano has a growing reputation for contemporary art

Visit This

Twin central squares — Piazza della Cisterna and Piazza del Duomo — are the heart of the town.

Dominating the latter is the Collegiata (a “collegiate church”, essentially a cathedral without a bishop’s seat), whose interior walls are covered in frescoes. The earliest date to the medieval period, and are in the Sienese–Gothic style. They recount narratives from the Old and New Testaments, including a lurid “Last Judgement” by Sienese painter Taddeo di Bartolo above the main door that’s reminiscent of an episode of “The Walking Dead”.

At the far end of the nave, the Cappella di Santa Fina is a harmonious Renaissance collaboration between sculptor Benedetto di Maiano, architect Giuliano da Maiano, and painter Domenico Ghirlandaio.

The latter’s pair of frescoes include fascinating detail relating to the town and the legend of its saint, Fina. As she is dying, flowers spontaneously bloom on the plank where she lies. On the left-hand wall, angels hover around the city’s towers ringing bells in her memory. A few of the town’s sights still close, to remember their little 13th-century saint, each March 12.

Nearby, the painting collection at the Museo Civico is fairly small, but its quality testifies to the artists that passed through San Gimignano in its heyday. The centrepiece is a “Maestà” (Virgin Mary surrounded by saints) painted in 1317 by Lippo Memmi, and finished fifty years later by Bartolo di Fredi. Upstairs are works by Coppo di Marcovaldo, Benozzo Gozzoli, Filippo Lippi, and Pinturicchio. After you have seen the art, you can climb the 54m Torre Grossa for views that stretch for miles.

San Gimignano

Moving way along the historical timeline, San Gimignano has a growing reputation for contemporary art. The Galleria Continua is a disorientating, warren-like space that often showcases the work of major names such as Antony Gormley.

Florentine International Gothic painter Benozzo Gozzoli worked on several projects in San Gimignano. He was commissioned in 1464 to paint an allegorical fresco on the walls of Sant’Agostino, celebrating St. Sebastian (the traditional saintly protector against plague, which was a regular and devastating visitor to the town during the Middle Ages).

The Augustinian monks liked his work so much that Gozzoli returned to the church to paint the apse chapel with “Scenes from the Life of St. Augustine”.

Eat & Drink This

The longest queues in San Gimignano aren’t for a church or museum, but for the modern artisans at Gelateria Dondoli, more often known as Gelateria “di Piazza” after its location on San Gim’s prettiest square. Ice-cream flavours range from the traditional to weird and wonderful combos, like “Rosemary’s Baby” (raspberry and rosemary), crema di Santa Fina (made with saffron), blackberries and lavender, or zabaione con vin santo (custard with Tuscan sweet wine).

San Gimignano is at the centre of the growing zone for Tuscany’s only dry white DOCG wine, Vernaccia di San Gimignano. This straw-coloured, light white wine has a provenance that dates at least to the 1200s. The Museo del Vino Vernaccia di San Gimignano offers tastings and displays on the wine’s history.

The Great Outdoors: Wildflower Walks

There are several fine rural walks around San Gimignano, through the vines and olive groves that approach the town on all sides, or among the wildflowers in spring and early summer. Take a good trail map, or contact the San Gimignano tourist office to book a guided half-day walk.

San Gimignano

Three Excursions from San Gimignano

  • Florence: it’s easily accessible by car, and has enough art and culture to keep you busy for a year
  • Colle Val d’Elsa: for a quiet, Gothic Old Town and fine hand-painted ceramics
  • Monteriggioni: for its perfect, intact ring of 13th-century defensive walls, which were even mentioned in Dante’s “Inferno”

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