Villas in the Valdelsa

The Elsa valley is one of the most beautiful parts of Tuscany. Once a crucial part of the "Via Francigena" (The Frankish Route) that linked Rome to Northern Europe by pilgrimage and trade, the valley's fortunes rose in the 8th century, when the Lombards (think Charlemagne) realised that the Elsa valley is protected by a range of hills from the mediterranean coast, which at that time was still controlled by the Byzantine navy operating from Constantinople. Because of this protection the valley became a thoroughfare of trade and pilgrimage that made the fortunes of cities like Siena, and many of the other smaller towns on this route.

Read our guide to the Val d'Elsa

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italy > tuscany > florence


Sleeps: 12
€ 2851 - € 5067 per week.

italy > tuscany > siena


Sleeps: 16
€ 8107 - € 9577 per week.

italy > tuscany > pisa

Villa Amorosa

Sleeps: 14
€ 4000 - € 5500 per week.

italy > tuscany > siena


Sleeps: 8
€ 1257 - € 2543 per week.

italy > tuscany > siena

Dan's House

Sleeps: 4
€ 800 - € 1067 per week.

italy > tuscany > pisa


Sleeps: 12
€ 4556 - € 6174 per week.

italy > tuscany > siena


Sleeps: 6
€ 1038 - € 1851 per week.

Guide to the Val d'Elsa

The Valley
Historical Notes
Local Events
Things to Do
Towns and Sites
Food and Wine
Market Days

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.

Farming the Val d'Elsa 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 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

Palio of Casole d'Elsa

On the 2nd Sunday of July jockeys mount their horses for Casole’s bareback horse race up the hillside leading to the village. In each of the six contrade, or town quarters, celebrations spill into the streets, so come along and join the party. Local villages all participate and there is dancing, eating and drinking over the weekend.

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

Cristallo tra le mura

Glass blowers are on display throughout the upper historic centre of the town that has been producing crystal for the past 800 years. The blowpipe, essential tool for glassblowing was originally invented by Syrians - the Roman empire embraced the technique and applied it with great flare to a wide variety of art forms. During the Middle Ages the knowledge largely disappeared, save for some centres, like Venice and Colle val d'Elsa, which kept the knowledge alive.

Mercantia Street Art Festival in Certaldo – 15-19 July 2020

Mercantia street festival

This colorful international street festival offers evenings of music, artisan ware, and costumed performances in the upper historic centre. For five evenings the medieval town is brought to life by singer-storytellers, tightrope walkers and trapeze artists who defy gravity, clown and marionette shows, acrobats who perform to jazz music, itinerant bands who dance through every corner of the town, dancers, trampoline performers and artists who “play with fire”—literally. A great experience and worth seeing.

Il Pigio in Poggibonsi – Early October

Pigio grape pressing

In harvest season, the 7 districts of Poggibonsi compete to see whose grape-pressing produces the most juice to win a decorated demijohn. This has been gaining in popularity over the last few years - it's a great big town get-together to celebrate the grapes and wine of the season. The dates vary according to the year - in 2019 it was on the last weekend of September.

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

Ferie delle Messi

This medieval harvest & fertility festival commemorates those dating back to 1255 where knights competed to augur abundant harvests. The "Knights of St. Fina" have organised the event since 1993 with the objective of celebrating the honor of the knights of San Gimignano that took part in the famous Tuscan Battle of Montaperti (1260) and Campaldino (1289), as described in ancient documents.

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

Memoriae di Semifonte

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: artists, flag bearers, musicians and jugglers bring alive the medieval atmosphere, while visitors can enjoy the atmosphere.

Radicondoli Festival in Radicondoli – late July to early August

Radicondoli festival

Days and nights of music and theatre in a hilltop village with some of the best scenery around make this a much-loved festival. Once home to the famous composer Luciano Berio his legacy has been an excellent music school and this festival of music, theatre and more.

Sagra del Fungo in Pievescola – first 3 weeks of September

Mushroom festival

In the first 2 weeks of September Pievescola organizes a favourite local event, the Sagra del Fungo, a culinary celebration dedicated to the wonderful Porcini mushroom found in the area. Dancing, local and wine and mushrooms in more ways you can imagine. This mushroom extravaganza is a local favorite event honouring Porcini mushrooms.

Medieval Festival in Monteriggioni – 5-14 July 2019

Medieval festival

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. Everybody is in medeival dress and you must exchange your money at the town gates for Florins - or similar. With the town entirely lit by torch-light this is a very atomshperic event.

TartuFesta in Montaione – 21, 27 & 28 October

Truffle festival

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. An Autumn Festival that celebrates a territory rich in agricultural produce: wine and cheese, cold cuts and extra-virgin olive oil, saffron and honey, and above all the White Truffle, that finds here its natural environment.

Ca’Stellare Palio in Castelfiorentino – 28 – 30 June

Ca'Stellare Palio

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

The events include a "Palio dei Bambini", an event designed with children in mind who can compete for their very own "Palio".

Calici sotto le Stelle in San Gimignano – 10 August

Sotto le Stelle

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

San Gimignano Opera Listen to opera from the cathedral steps in San Gimignano Estate, the 3-month summer series of concerts, from opera arias to sacred music, that aim to delight both connoisseurs and newcomers to classical music. Italian and international singers and pianists perform in this magical town in the heart of Tuscany.. List of town’s events

Crystal Museum 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. The museum is in underground rooms once occupied by one of the furnaces of one of the towns 18th century crystal manufacturers . There is a collection of pieces from the pre-industrial era, but also some dating back to the 14th and 15th centuries.

Archeodromo 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. The old fortress was the pride of the town until conquered by the Florentines and is a fantastic place to explore today.

Galleria Continua 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. Founded in 1990 by Mario Cristiani, Lorenzo Fiaschi and Maurizio Rigillo, with the intention to give continuity to contemporary art in a landscape rich with the signs of ancient art.

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.

SentierElsa Following the SentierElsa trail along the river Elsa

Towns & Sites

Casole d'Elsa

Casole d'Elsa

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.

San Gimignano

San Gimignano

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

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.



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.

Barberino Val d'Elsa

Barberino Val d'Elsa

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

Risotto allo Zafferano 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.

Crostino Nero 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.

Brasato al Chianti 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 Porcini mushrooms amassed by jealous collectors or Carciofi, the flexible artichoke that may be marinated, fried or stuffed.

Tiramisu 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.

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