Europe holidays: Exploring the medieval hill town of San Gimignano, Tuscany

The romantic Tuscan town of San Gimignano. Photo / Getty Images

Perhaps I have the haunting look of a pilgrim. Footsore and parched, I have walked the 3km semi-circle around the double walls of San Gimignano from the southwestern gate of San Giovanni to the northeastern Porta delle Fonti. After skidding down a rocky, dirt path, I dust myself off next to the stone-arched vaults of the 12th-century washhouse, once used for drawing water and washing linen.

A Spanish hiking party is picnicking along the stone edge of this medieval font with its chain of arcaded pools and shadowed, spring-fed grotto. As an offering to a fellow traveller pulsating from the midday Tuscan sun, I'm presented with a glistening wedge of watermelon.

Tuscan hillside surrounding San Gimignano. Photo / Marian McGuinness

I savour its cooling sweetness in the shade next to the vegetable garden of a stone villa that tumbles into the Chianti countryside. This is quintessential Tuscany. The villa’s backyard is an art installation of fig trees, grape vines and tomato bushes splashed with zucchini flowers. A clothesline, strung between two olive trees, is pegged with large navy and white underpants. They catch the breeze like bunting, flickering shadows on the dry, clay ground.

This isn’t what I had expected on my walk around San Gimignano, the once-Etruscan hill town that sits like a crown above the Val d’Elsa, equidistant between Florence and Siena. It’s built on the Via Francigena, similar to Spain’s Camino de Santiago; this pilgrims’ route became a stopover for 10th-century merchants and wayfarers walking from Canterbury Cathedral in England to the Vatican in Rome.

Named in honour of St Geminianus, a Bishop of Modena who defended and saved the town from barbarian hordes, San Gimignano is often described as the Medieval Metropolis, or the Town of a Thousand Towers. Legends evoke stone towers swaddled in gold. Possibly, the ‘gold’ was a metaphor for saffron, the purple flower with vivid golden-tipped crimson threads dried for seasoning and food colouring. San Gimignano was the major Italian producer of saffron and its export made the town wealthy.

San Gimignano, the once-Etruscan hill town, sits above the Val d'Elsa, equidistant between Florence and Siena. Photo / Getty Images

Until the 14th century, tower-building kept warring families busy as they tried to outdo each other, perhaps in the style of Shakespeare’s Montagues and Capulets. The Black Death in 1384 ended their empire building. The town’s 72 towers fell into disrepair as three-quarters of the 13,000 townsfolk died. Nearby Florence bullied the town into submission and rerouted the pilgrims. San Gimignano became a town suspended in time; a town where 21st-century tourists have become the new pilgrims.

Medieval tower in San Gimignano. Photo / Marian McGuinness

Today, as I wander the pedestrian-friendly streets, it’s a game of hit and miss as I dodge the selfie-generation snapping themselves in front of the remaining 14 honey-stoned high-rises. Many towers have small shrubs and weeds growing in their chinks, but only one, the 54m tall Torre Grossa with its 230 steps, located in Piazza del Duomo, is open for climbing. Unlike the circular stairwells of other hill town towers, this one has a wide metal stairway interspersed with landings where you can rest and catch your breath. The last section is a little awkward as you climb a steep ladder of 15 rungs before popping through a narrow opening at the top. The view across the rows of umber-tiled roofs and the panoramic view of the undulating Chianti countryside is worth the thigh-tightening exercise.

Exploring the pedestrian-friendly back streets of San Gimignano. Photo / Marian McGuinness

As you would expect of this romantic Tuscan town, the main street is touristy, but there are hundreds of secret corners, with dark arches and tiny alleys, waiting to be explored. If you’re interested in ceramics there are plenty sporting sunflowers, bountiful fruits and Tuscan hill scenes. If I could have wheeled one of their table tops home, I would have.

Taxidermied wild boars greet you at several shop entrances. Lethally tusked and motley-bristled, their shiny, tiny piggy eyes invite you to buy a net of wild boar salami with truffle, a couple of trotters, or a hairy flank. Further into the Aladdin’s cave of gourmet goods you can pick up a bottle of one of Italy’s finest white wines, Vernaccia di San Gimignano, tempting wedges of pecorino and local honey to drizzle over it. Just add some crusty bread and head off to the hillside for a Tuscan picnic.

With its small, historic nucleus and virtually traffic-free streets, San Gimignano is ideal for strolling. The two main boulevards, Via San Matteo and Via San Giovanni, criss-cross the town. They link the enchanting squares of Piazza della Cisterna, Piazza Duomo, Piazza Pecori and Piazza delle Erbe, where art galleries, enoteche (wine shops) and atmospheric cafes, offering handmade pici (thick, hand-rolled pasta) with wild boar ragu, line their manicured streets.

Ceramic delights in San Gimignano. Photo / Marian McGuinness

There are must-see churches, palaces, museums, and even a medieval hospital dating back to 1203. Had I been squeamish, I might have walked past the Museo della Tortura (Museum of Torture) in the Torre del Diavolo (the Devil’s Tower), but the macabre blurb on its poster “these instruments show just how much human fantasy knew no limits” reels me in, hook, line and tongue-cutter.

Not too far inside the first cold stone and brick cavern, reality sobers me to the horrors of human cruelty. It puzzles me to think of the hours of creativity that went into designing and delicately decorating these devices of humiliation, oppression and torture. Take the iron sandals with the bell at the toe that was fitted to clumsy servants. Every time the bell rang, the master tightened the heel.

There are many gruesome original and reproduced items on display that reflect a time in history when public hangings and punishments were seen as entertainment.

No detail is spared in the explanation of how each instrument worked, which orifice the device was meant for, which limb was dislocated and who was the usual customer. Women are particularly well represented in the museum with breast rippers, shrew's fiddles and scold's bridles complete with tongue depressors, that made talking painful.

Some may think that the idea of a visiting a torture museum is no better than attending the public spectacle of torture in the past. Yet it’s the professional display and insightful explanations that make me question how civilised we are meant to be today.

Back out in the light, the stumble-upon-places in the back streets give San Gimignano an even richer dimension.

Veering off the main street and heading along Via San Matteo, I come to a quiet, grassy square and the unassuming 13th-century church of Sant’ Agostino. Its terracotta floor and rose window are complemented by the 17-panelled fresco cycle around the high marble altar depicting the life of Saint Augustine.

At a clutch of nearby shops, a door framed by photos of the Tuscan countryside draws me inside. The owner is working at his desk. Behind him are award-winning photographs that I remember seeing in the newspapers back home: barn owls, a bat skimming water and a kingfisher catching its prey.

The man is wildlife photographer, Claudio Calvani, winner of more than 250 awards, and celebrity photographer of Tuscan calendars and spreads in National Geographic. He generously shows me his work, flicking through photographs of cypress-lined hills and rolling fields of sunflowers. “The best light is in October and November,” he tells me. The colours of each season are so vibrant, that I ask if he used filters when photographing them. “Only with three,” Claudio confesses. “The rest are a gift of the Tuscan sun.”

Tuscan photographer Claudio Calvani in his studio. Photo / Marian McGuinness

The heat of the day calls for gelato and I head back to the heart of the town to the triangular Piazza della Cisterna, named after the fountain at its centre. For hundreds of years this town centre bustled with markets, tournaments and roving minstrels. It was also the site of two of Franco Zeffirelli’s films: the story of St Francis of Assisi - Brother Sun, Sister Moon and the semi-autobiographical Second World War drama, Tea with Mussolini. With its filmic beauty, San Gimignano has become one of the most cinematographic locations in Tuscany, with more than 30 movies to its credit.

The lines are four-deep inside neon-signed Gelateria Dondoli, the four-times Gelato World Champions. From the landscape of pastel mounds topped with fruit, chocolate, nuts and berries, it’s decision time: champagne, cinnamon, panna cotta, or the twin-flavoured, saffron and pine-nut or spumante and grapefruit. The walls are lined with testimonials from actors, artists and politicians. A 1993 photograph signed by Russian novelist Alexander Solzhenitsyn, hangs next to an ageing travel article where owner, Sergio Dondoli boasts, “an Italian is born to gelato. The secret is to be curious. I even made shrimp gelato once.”

Lining up for a famous gelato. Photo / Marian McGuinness

The medieval towers cast criss-crosses over the piazza as the sun lowers. I indulge in the beauty of the backdrop beyond these Tuscan walls of San Gimignano: the watercolour hills, the combed vineyards and the undulating lines of cypress.

With my waffle cone of fig and passionfruit gelato glistening, I imagine medieval pilgrims, en route to Rome, resting here in the shade and wishing they too were supping on this delectable gift from the gods.

See more at Visit Tuscany.