Gentle hills dotted with olive trees, vineyards and the ever-present cypresses, centuries-old woods, cities of art and villages that have stood the test of time, majestic abbeys and dirt roads: if you choose to spend a holiday in Siena or its surroundings, you certainly won't be disappointed. Here, in the heart of Tuscany, between Chianti, Val d'Orcia, the Crete Senesi, Val di Chiana and Val d'Elsa, nature and history merge to create a unique landscape in the world and give a sense of deep wonder in those who decide to discover it.
From Siena, considered the absolute incarnation of the medieval city, we then leave for its hills to find out what to see.
Holidays in Siena and surroundings: places not to be missed
We can only start from here. Siena, famous for its Palio, is a real jewel of the Italian Middle Ages. Its main square, Piazza del Campo, is one of the most evocative places in the city and in the whole world. Precisely in this setting, the famous Palio race takes place every year, an event that attracts tourists from all over the world.
But it is not only Siena that deserves a visit: the area surrounding this city and its hills offer other attractions that are worth exploring, many of which are located along the ancient and suggestive Via Francigena.
San Gimignano, the "city of beautiful towers
The two best-known cities in Italy - and in the world - for towers are Bologna and San Gimignano, to the point that both boast the nickname "Manhattan of the Middle Ages". In short, you have already figured it out: if you decide to see this city, a visit to one of the current 15 towers – originally it seems there were 72 – is absolutely a must: you will see them soaring already many kilometers away.
It is no coincidence that the "city of beautiful towers" was included in the UNESCO list of World Heritage Sites in 1990.
This village - today considered one of the most beautiful in all of Tuscany - had its period of greatest splendor in the first three centuries after the year 1000, due to its strategic geographical position: it is one of the main rest stations on the Via Francigena, which in the early Middle Ages became the itinerary of pilgrims. And in fact, as soon as you enter one of the two entrance doors, you will feel catapulted into an atmosphere where time seems to have stopped.
From the wonderful Piazza della Cisterna, whose name is due to the presence of the large medieval cistern dating back to 1200, to the Torre Grossa from which you can admire the beautiful panorama of the surrounding hills, up to Piazza del Duomo or Piazza delle Erbe: every corner or alley of San Gimignano deserves to be discovered by savoring this suspended medieval atmosphere. For the most curious - and courageous - the Museum of Torture certainly deserves a visit, which will be a real journey into the era of the Inquisition. Those who want something more "quiet" shouldn't miss the marvelous frescoes of the Cathedral and the Church of Sant'Agostino, without forgetting to visit the masterpieces preserved in the Civic Museum of the Palazzo Comunale.
A walk on the walls of Monteriggioni
From the turreted city to the… fortified city! Just 20 km from Siena there is another treasure that absolutely deserves a visit: it is Monteriggioni, located on a hill and famous for its powerful and perfectly preserved medieval city walls. About 570 meters long, with 14 still intact towers and two gateways, the walls surround the entire village, offering a spectacular view of the surrounding Tuscan countryside. It is no coincidence that Dante himself was struck by it, mentioning the village in the thirty-first canto of the Inferno, «Come in sulla Cerchia Tonda Monteriggion di torri si corona».
In short, even in this case, entering Monteriggioni is equivalent to taking a dive into the past. If a visit to one of the countless towers is a must for San Gimignano, here you cannot miss a walk on the walls. Then, you can dedicate yourself to discovering the alleys that wind from Piazza Roma, the main square of the town overlooked by the Pieve di Santa Maria Assunta church in perfect Gothic style.
San Quirico d'Orcia and Bagno Vignoni, in the heart of the Val d'Orcia
Not far from each other, there are this two villages: Bagno Vignoni and San Quirico d'Orcia.
You will certainly have heard of the first, especially for what is considered one of the most beautiful and particular squares in Italy. The reason? The town grew up around an imposing basin of medieval origin, in which thermal water still flows at 52°C, overlooked by magnificent Renaissance buildings. In fact, Bagno Vignoni is famous for its thermal baths, and during the Renaissance it was a very popular holiday destination. From the central square, the thermal water then goes to the suggestive Parco dei Mulini, a unique work of hydraulic engineering.
Just 8 minutes by car, here is San Quirico d'Orcia, with a strategic position for visiting the splendid Val d'Orcia, whether on foot for trekking enthusiasts, by car or even by motorbike. From the historical center contained but full of charm, the only way to discover this pearl of Tuscany is to get lost in its alleys and stone houses. You will come across the Pieve dei Santi Quirico e Giulitta, also known as the Collegiata, a church in Romanesque style on the outside and Baroque on the inside, and next to the Palazzo Chigi, which now houses the town hall. It is also worth visiting the Church of San Francesco, also known as the Church of the Madonna, as it houses the terracotta statue of the Madonna, by Andrea della Robbia.
A dip in the natural thermal baths of Petriolo
We remain in topic "spas" and follow the course of the Farma river, along whose banks and surrounded by luxuriant woods a treasure is hidden. They are the Terme di Petriolo, the closest free spa to Siena and of very ancient origin: it seems in fact that they were already known in Roman times and were then frequented by some of the most illustrious personalities of the past. Here the thermal water flows to the surface at a temperature of around 43°C and collects naturally in small pools with different temperatures, ideal for alternating hot-cold routes.
On the trail of the legend at the Abbey of San Galgano
Leaving aside the countless villages that, from Siena, you can pass along the road, here is another pearl to discover. Because just 24 km from Siena, the legend of King Arthur, of the knights of the round table, but above all… of the sword in the stone comes to life! Where? Precisely in San Galgano, where stands an imposing basilica built in 1218 with a Latin cross plan with three naves, 72 meters long and 21 wide, which has a unique feature: the external skeleton of the walls is still intact, while the roof is missing. And not far from the Abbey, there is the Hermitage of Montesiepi, where, according to legend, San Galgano lived as a hermit for the last year of his life and where there is a sword stuck to the hilt inside a stone...... In short, believe it or not, this place has a mystical aura that will take you back in time.
A glass of Brunello in Montalcino
Discovering the wonders of the Sienese hills also means savoring its tastes, flavors, food and wine traditions. And what place contains this concentration better than Montalcino, the birthplace of one of the most famous Italian wines, Brunello? The village stands on a hill dominated by the spectacular fourteenth-century fortress and is surrounded by medieval walls. After a visit to the city, however, among artisan shops and marvelous palaces and churches, you cannot leave without having tasted a glass of this precious wine.
Moving outside the city, in the Castelnuovo dell'Abate area, an area known for the particular elegance and balance of the grapes, stands Tenuta La Poderina, which will allow you to try the experience of a tasting of the excellent wines of the area, such as the Rosso or the Brunello di Montalcino or the Moscadello di Montalcino.
The Sienese hills are therefore an enchanting place full of places to visit. From the city of Siena, to abbeys and wine cellars, up to excursions into nature, there is something for everyone.
Do you already have in mind when to leave?