Val d’Elsa

our guide to the val d'elsa

the valley

If the geography of this valley was shaped by a tributary of the Arno, the Elsa River, which flows through the provinces of Siena, Poggibonsi, Florence and Empoli, its generous character was also influenced by the ancient Via Francigena, the pilgrims’ route from France to Rome.  The wide gently-rolling landscape became a crossroads of human and commercial exchange that continues to the present day, while its fertile terrain and forests still produce the ingredients – truffles, mushrooms, grapes, olives – that feature in in all Tuscan menus. 

The beautiful walled towns fought over in the Middle Ages are wonderful places to explore.  Though lesser known than nearby Florence or Siena, their preserved centres are immediately evocative of historic moments in time.  That they also speak of the authentic daily life of Tuscany with weekly markets, local festivals and evening strolls along the main street further makes this a winning destination.

The wide valley of the Elsa River and the important medieval towns that grew up within it

historical notes

Saint Geminianus, namesake of the 'Town of Fine Towers' San Gimignano

Though many necropolises indicate that this was an important centre of Etruscan civilization, the Valdelsa came into its own during the Middle Ages.  Along the Via Francigena merchants, bankers and pilgrims traveled and by the mid-13th C. had up to 34 guest houses or inns in which to stop over.  The tenure of life in this period is wonderfully illustrated in the Decameron, whose author Giovanni Boccaccio was born and lived in Certaldo.

So attractive was this valley that towns had to put up walls to defend themselves from both Florence and Siena whose rivalry and warfare complicated the life of valley residents.  An excellent example is Monteriggioni, the tiny fortified village mentioned in Dante’s Inferno, whose cornet of 14 towers at least allowed them to see whose troops were headed their way.

Some towns have been more fortunate – legend has it that San Gimignano was saved from destruction at the hands of Attila the Hun in the 5th C. by the Bishop of Modena Saint Geminianus; the towers and frescoes were again saved –  according to Zefferelli’s film Tea with Mussolini– from the dynamite of retreating German troops by a group of English women.  Whether either is true, the town’s historic centre gained UNESCO status as a World Heritage Site in 1990 and this may once save it for the future.

events in the val d'elsa

Palio in Casole d’Elsa – 2nd Sunday of July

Jockeys mount their horses for Casole’s bareback horse race up the hillside leading to the village. Celebration follows and all are welcome.

Cristallo Tra Le Mura in Colle di Val d’Elsa – early September

Glass blowers are on display throughout the upper historic centre of the town that has been producing crystal for the past 800 years.

Mercantia Street Art Festival in Certaldo – 10-14 July 2019

This colorful international street festival offers evenings of music, artisan ware, and costumed performances in the upper historic centre.  

Il Pigio in Poggibonsi – Early October

In harvest season, the 7 districts of Poggibonsi compete to see whose grape-pressing produces the most juice to win a decorated demijohn.

Ferie delle Messi in San Gimignano – 3rd week of June

This medieval harvest & fertility festival commemorates those dating back to 1255 where knights competed to augur abundant harvests.

Memoriae et Historiae di Semifonte in Barberino Val d’Elsa- early June

The entire community of this medieval town turns out in costume to honor Semifonte, destroyed by Florence in 1202. The commemoration is, however, also joyous with music, artisans and flowing wine and food.

Radicondoli Estate in Radicondoli – late July to early August

Days and nights of music and theatre in a hilltop village with some of the best scenery around make this a much-loved festival. 

Sagra del Fungo in Pievescola – first 3 weeks of September

This culinary celebration is a local favorite event honouring Porcini mushrooms. Dancing, wine and Porcini in more ways you can imagine.

Medieval Festival in Monteriggioni – 5-14 July 2019

This small village, a ‘crown of towers’, is the ideal setting for a medieval fair – banquets, games, music and artisans re-awaken the Middle Ages. 

 displayTartuFesta in Montaione – 21, 27 & 28 October

White truffles are the star of the show – cooked, exhibited and sold – but other food of the Valdelsa are suitably featured in this hilltop festival.

Ca’Stellare Palio in Castelfiorentino – 28 – 30 June

The 9 contradas or town districts compete in races and parades of chariots to win the cencio, or drapery, painted by a local artist.

Calici sotto le Stelle in San Gimignano – 10 August

A night of wine and starlight raises a glass to San Gimignano’s famed white Vernaccia wine as well as local reds on the ‘Night of San Lorenzo’, known for its display of shooting stars

things to do in the val d'elsa

Visit the Museo del Cristallo in Colle di Val d’Elsa and be ready for a bit of sparkle. In a town that produces 95% of Italy’s crystal and 15% of the world’s, this museum helps to explain how.

Listen to opera from the cathedral steps in San Gimignano Estate, the 3-month summer series of opera, poetry, theater, ballet and concerts in Piazza del Duomo. List of town’s events

Introduce children to the Middle Ages at the Archeodromo in the Parco della Fortezza Medicea in Poggibonsi. A on-going medieval settlement brought to life – fun & educational. 

Get to know the Elsa River by crossing it and walking along its banks.  The SentierElsa trail starting from Colle di Val d’Elsa is a wonderful woodland path, fascinating for the whole family.

Enjoy a modern antidote to too many ancient stones in San Gimignano’s Galleria Continua.  This important contemporary art gallery has partners in Beijing, Havana and Les Moulins.

Following the SentierElsa trail along the river Elsa

towns & sites

casole d'elsa

san gimignano

This lovely hill town looks down on a patchwork of greenery and despite its small size has a lively village life with an art centre, restaurants, enoteca, ancient castle and friendly residents easy to interact with.  There are concerts in the Romanesque Collegiata & festivals year round.

A UNESCO World Heritage Site, San Gimignano has an unmistakeable skyline.  Only 14 of the original 72 towers remain but they easily evoke the Middle Ages.  Fine arts, famous gelato, leather works and lively music throughout the year draw visitors to its winding stone streets.

colle val d'elsa


Colle di Val d’Elsa grew to prominence thanks to its position along the Via Francigena.  The upper historic part of town is a well-preserved medieval centre, with a Michelin restaurant named after native son Arnolfo di Cambio. A lower industrial area continues its famed crystal production. 

An ancient Tuscan hill town of about 1,000 inhabitants, Radicondoli maintains much of the 13th C. look it had when people left villages and castles to find security within its walls.  Now shopping, restaurants and open-air dancing are what draws visitors to its lively centre.



Built on its hillock in 1213 by the Sienese, Monteriggioni is undoubtedly the most classic fortified town in Tuscany.  Its walled crown of towers is encircled by olive groves and one has but to step within its gates to feel what it would have been like to live on a small scale.

In the Lower Valdelsa, halfway between Florence and Pisa, Castelfiorentino takes its name from the fortified castle on the Via Francigena,  Though devastated in 1521 by the Spanish, masterpieces survived in its many churches and neighboring villas.


Barberino val d'elsa

The birthplace of Boccaccio, the fascinating upper medieval portion of Certaldo is reached by foot or cable car.  Built almost entirely of brick, the centre includes the house of the poet and a striking Palazzo Pretorio and during the Mercantia Street Fair joyously comes to life. 

On the ancient winding Via Cassia Barberino Val d’Elsa sits high above the valley and close to the Chianti region that ensures the wine brought to its tables are of excellent quality.  Risen from an ancient city destroyed by Florence in 1202, town life hums on its one beautiful street between ancient gates.

food and wine

Some beloved Valdelsa recipes feature ingredients that thrive in the river valley – The woods around Montaione and nearby San Miniato  are famous for their tartufi bianchi, white truffles, a prized item that finds its way into pastas, omelettes and scattered over slices of beef.  Saffron has been one of the crown jewels of San Gimignano for centuries and it gives colour and delicate taste to Risotto allo zafferano, pastas and even liqueurs.

Yet this down-to-earth region makes use of every part of what comes to their kitchens.  A paste of chicken livers, capers and a few fresh herbs grace toasted bread for the popular Crositini neri.  Leftover bread and garden tomatoes produce Panzanella, the cold first course that begins many summer meals., or the warm variation Pappa al pomodoro.  The Tuscans, like all Italians, love their beans and Paste e fagioli, the hearty soup of short pasta and beans is a local favourite.

Being so close to the Chianti region results in many cuts of meat – beef or even wild boar – being braised or slowly stewed in red wine to produce Stracottoor Brasato al Chianti.  A variation of this stew adds a head of garlic and a generous amount of pepper to produce Peposo.  To accompany main courses popular side seasonal dishes feature Porcinimushrooms amassed by jealous collectors or Carciofi, the flexible artichoke that may be marinated, fried or stuffed. 

To finish on a high, Tiramisù, literally a ‘pick me up’, is the ubiquitous cold coffee-flavoured dessert consisting of coffee-drenched ladyfingers layered with a whipped mixture of eggs, sugar and mascarpone cheese flavoured with cocoa.  No wonder it’s the dessert of choice.

Wines:  To accompany these dishes in the Valdelsa, one is particularly fortunate.  Not only do you rub shoulders with the Chianti region and all of its glorious red wines, but in the heart of the region San Gimignano produces a much-esteemed Vernaccia white wine.  Don’t forget, however, to finish the meal with Vin Santo, the ‘holy wine’ made from selected Trebbiano or Malvasia grapes that are dried, pressed and matured in wooden barrels.  

Crostini neri
Risotto allo Zafferano
Brasato al Chianti

market days

MONDAYS – Casole d’Elsa (1st & 3rd), Radicondoli (2nd & 4th)

TUESDAYS – Empoli, Poggibonsi, San Miniato, Gambassi Terme, Montespertoli

WEDNESDAYS – Barberino Val d’Elsa, Certaldo

THURSDAYS – Monteriggioni, San Gimignano, Empoli

FRIDAYS – Colle di Val d’Elsa, Montaione

SATURDAYS – Castelfiorentino, Certaldo, Staggia, Montespertoli


  • Osteria Casolani– Casole d’Elsa, Tel: +39 0577 948733
  • La Pergola– Radicondoli, Tel: +39 0577 790717
  • Il Granaio – Radicondoli, Tel: +39 0577 550791 or 393 1033287
  • Bar dell’Orso – Monteriggioni, Tel: +39 0577 305074
  • Osteria Antico Travaglio – Monteriggioni, Tel: +39 0577 1651764
  • Ristorante Arnolfo – Colle di Val d’Elsa, Tel: +39 0577 920549
  • L’Antica Trattoria – Colle di Val d’Elsa, Tel: +39 0577 923747
  • Le Vecchie Mura – San Gimignano, Tel: +39 0577 940270
  • Osteria del Vicario – Certaldo Alto, Tel: 0571 667809
  • La Mangiatoia – San Gimignano, Tel: +39 0577 941094
  • C’era una Volta – Lucardo, Montespertoli, Tel: +39 0571 669578

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