MEDIEVAL SIGHTSEEING
PIENZA
The name of the town comes from Pope Pius II, who was born here, and it means the city of Pius. Upon his election (1458), the pope wanted to transform his birthplace (back then an anonymous village of Corsignano) into the ideal Renaissance town; with this goal he hired the architect Bernardo Rossellino. The construction of Pienza started around 1459 on top of the ancient hamlet and took about four years, creating as a result a harmonious fifteenth-century town. The untimely death of Pope Pius II put a stop to the urban re-organization of the new city, which has remained practically unchanged over the centuries and represents a superb example of Renaissance architecture till today.
Today, the old town is a pedestrian zone with Piazza Pio II as the hub, surrounded by Pienza’s key monuments. The clear dominant is the Cathedral of Santa Maria Assunta, which towers over all the other buildings – a way to confirm the dominance of church over municipality. The cathedral’s size was ambitious, bringing some structural issues that are clearly visible around the main apse: it seems as if part of the cathedral was “losing ground” …
If you need a bit of calm, enter the Palazzo Piccolomini (on your right if facing the cathedral) and walk through it to the gardens designed back in the 15th century to celebrate the views of the valley. The gardens feature a fountain full of fruit garlands and four large rectangular flower-beds decorated with a half-moon, keys and a tiara – forming Piccolomini coat of arms.
Pienza is an ideal place for a stroll, be it romantic or with family & friends. Make sure you find your way to Via del Casello – a small street on the ramparts with unbeatable views of Val d’Orcia. You will see it all: Monticchiello, Radicofani, Monte Amiata, Castiglione d’Orcia… the winding roads lined with cypresses and olives, rolling hills changing color with the season… and if your eye-sights is close to excellent, you may even spot our agriturismo :-) you can enjoy an aperitif here or get a few scoops of ice-cream (try gelaterie Fredo Il Gelato Artigianale). Or just feel good hand-in-hand with your loved ones in the close-by streets of Via del’Amore (Street of Love) or Via del Bacio (Street of Kiss).
Pienza is certainly one of the best places to taste the traditional pecorino toscano – local sheep cheese – in all its varieties of taste. In fact, Pienza is considered the “capital” of pecorino cheese, because of its high quality, which owes to the flavorsome and aromatic milk of sheep on pastures in Val d'Orcia. If you are lucky, you may experience the cheese festival in Pienza, when men compete in rolling round blocks of cheese toward a spindle – it is called the Fiera del Cacio and takes place in Aug-Sept.
Alternatively, take one of our bikes for a spectacular ride through the valley’s countless white roads with an ambition to make it all the way to Pienza (about 25 km one way). Recharge energy with a glass of Vermentino in the bar on the city walls before enjoying the ride back down.
MONTICCHIELLO
It is a small hill-top town, on the road between Pienza and Montepulciano. It is a picture-perfect place: it offers great views of Pienza and the whole Val d’Orcia, for which it is often referred to as “terrazzo della Val d’Orcia”. At the same time, it has the charm of a quiet medieval place with defensive thick walls and towers. While the hill has been inhabited already by the Etruscans and Romans, the prime time of Monticchiello was between the 13th and 15th centuries, when it served as a stronghold for the defense system of the Republic of Siena. After the fall of Siena in 1559, Monticchiellogradually lost its importance…
Why we like it today? It is best for a peaceful stroll without hordes of tourists, with sunset being a special time for spectacular vistas over the valley. You can still see 3 out of the original 17 towers, enjoy the many finely restored stone houses adorned by flower pots and little balconies, or admire the Church of Santi Leonardo e Cristoforo (dating back to the days of greatest prosperity, home to many frescoes from the Sienese school).
All in all, you get a tasteful combination of stone, flowers and views. Throw in the 2 fine-dining restaurants and a lovely cafe under the fig trees – you get a hidden gem.
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There is a place little out of town for taking one of the famous Tuscan pictures – the winding road coming from Montepulciano to Monticchiello. Stop by, we will be happy to show you on the map.
BAGNO VIGNONI
This village is a little bit different from the rest. By size, it is barely a smudge (population 30). However, it sits atop a natural hot spring, which attracted people ever since. The healing properties of local water were discovered by the Etruscans, used by the Romans and, during the middle ages, frequented by the Via Francigena pilgrims as well as some famous historical figures (for example Pope Pius II or Catherine of Siena).
In terms of sightseeing, the village catches one’s eye, too. First, the main square, named Piazza delle Sorgente (or the “Square of Sources”) is in fact a large pool from the sixteenth-century, 49 meters long and 29 meters wide, with volcanic water of constant temperature of around 50°C. Second, the village and the buildings around the plaza remained largely unchanged, despite various instances of war and destruction, bringing you back to the Middle Ages. Third, just outside the old town, short walk from the piazza, is the Parco dei Mulini, where in the past were a number of mills located along the river.
Today, it is prohibited to bath in the 16th-century tank. However, you may still enjoy the healing properties of the local water - either in one of the private spas or simply (and for free) by relaxing in the natural pools and little waterfalls of the Parco dei Mulini, which are fed from the same volcanic spring. So, make sure to pack (preferably old) swimming suite and a towel. As you sit in the warm pool, with a little mist coming up, it will be easy to imagine why this was one of the popular stops on the Via Francigena during the long Christian pilgrimage.
Via Francigena is the ancient pilgrimage route that in medieval times connected Canterbury (UK) to Rome and to the harbors of Apulia, where people could sail off to the Holy Lands (Terra Santa). Today, it crosses four countries: it starts in the UK, then crosses France and Switzerland before reaching Italy. In total it is 2089 km long, of this approximately 400 km take pilgrims through Tuscany. From our agriturismo, Bagno Vignoni is the nearest point for embarking on the route.
Interestingly, there never was an “official” road map that the pilgrims followed as they made their way south to the Terra Santa or to pray at the tomb of St. Peter and Paul in Rome. The Via Francigena was an un-codified path that gathered the walkers as they funneled into Italy from all over Europe. It was a conglomerate of many roads merging together for safety, convenience and hospitality. And it wasn’t until the discovery (in the 1980’s) of the travel journal by the Bishop of Canterbury (from 990), that it was possible to actually trace a very real route.
MONTEPULCIANO
The town rests atop a narrow chalky hill of Monte Poliziano, in a place where the Val d’Orcia and Val di Chiana meet. This position makes it postcard-perfect, with 360-degrees view of the classic Tuscan country-side – green waves of the hills and golden fields dotted with cypress trees.
Montepulciano is best explored on foot - the main road winding up the hill for 1.5 km, starting at the Porta Al Prato and finishing at the Piazza Grande, which is considered the "living room" of the town. Here you'll find Palazzo Comunale (the City Hall), which looks a bit like a castle with a clock bell tower rising in the centre it may remind you of Florence’sPalazzo Vecchio. Climb the tower for the fantastic views - climb is short, just be ready for a narrow passage and potentially crowds in high season.
In the piazza, there is a well where citizens once drew water (look at the top for the Medici coat of arms); today offering a really good spot for taking a picture and especially eating your ice-cream. The alternative spot for ice-cream-eating are the looooong stairs of the Duomo. The Duomo (or cathedral of Santa Maria Assunta from the 15th century) strikes you with its uncompleted facade, which is in stark contrast with rich decorations on most of the other buildings in town. If you need to cool down, you may want to visit the Palazzo Contucci, on the southeast corner of the piazza or Palazzo Ricci just 100m off the piazza north west. Both palaces are built atop vast wine cellars that are well worth a visit. A little oddly out of town, you find another architectural treasure of Montepulciano – the sanctuary of the Madonna di San Biagio.
And it gets even better, if you are in town for the wine - the famous and delicious Vino Nobile di Montepulciano. To see and feel the history of wine-making in this place, visit the Cantina do Ricci, the cellars of the Ricci family (a few steps away from the Piazza Grande, free of charge, no need to make any appointment) and admire what is probably one of the highest cellar ceiling, making people call the place "the Cathedral". If you also want to taste and buy, we recommend the Bottega del Nobile at Via Gracciano, about 100m from the lower gate to town (Porta Al Prato). Ask for Antonella. If you do not know which one to buy, you cannot go wrong with ABC winemakers Avignonesi, Bindella, Boscarelli, La Braccesca, Cesiro, Contucci. Exception might be a nice bottle of Il Macchione, Poliziano or Sanguineto.
But even of you are not exactly into all the palaces and churches, the town offers a beautiful walk and many hidden places with beautiful views. Our personal favourites are the tower of city hall (as mentioned above), the terrace of the Ricci Palace (free entry) offering views to the west and a tiny square on the ramparts between Via Delle Mura and Via DeiCacciatori, approximately mid-way up the main road on your left, offering views to the east and a bench, bringing tranquility into the hustle. Close by is also the best positioned parking in town, follow signs P6, rarely occupied by tourists (there are 3 levels, just in case the first one is occupied, go left up the steep hill into the dead-end street).
Ohh, and if you want to bring home some leather presents, this is the town. But there are many original shops of local artisans, just pop in for the look and inspiration.
SAN QUIRICO D'ORCIA
This little town with well preserved old town is our favourite spot for a stroll before dinner in one of its great restaurants (best bistecca Fiorentina ever). Plus, the cobbled-stone streets are less crowded here. San Quirico has one main street, via Dante Alighieri, where you can find the Collegiata of the Saints Quirico and Giulitta, a beautiful Romanesque church with Gothic and Baroque additions. The stone is pretty weathered and marked with holes; the doorways are beautiful. If you are in for a hunt, study the sculptures all around and notice that each of the lions guarding the various entrances is in different pose. If you are patient, you may even find two crocodiles.
On the via Dante Alighieri is also the Piazza della Liberta, heart of the small town, with the Church of the Madonna, which protects the terracotta statue of the Madonna that used to be in the nearby Vitaleta Chapel, one of the most photographed chapels in Tuscany. The last large church on the short street is the Romanesque Church of Santa Maria Assunta. It is very simple, with a typical open bell tower and wooden roof.
However, our favorite place in hot days are the Horti Leonini gardens, an example of the Italian Renaissance geometrical gardens. It has two entrances – one from the south, right behind the Santa Maria Assunta church, and one from the Piazza della Liberta.
Finally, if you drive out of San Quirico in the direction of Montalcino, you will find the famous groups of cypress trees. There are two distinct groups of trees, located on isolated hills overlooking the Via Cassia. Here are the coordinates: the first group of cypress trees is located at 43 ° 03'45.62 "N 11 ° 33'31.86" E, while the second group is along a dirt road at 43 ° 03'38.99 "N 11 ° 33'30.49" E. The best way to enjoy the typical views is probably on foot or on bike, in spring or early summer. But don’t worry! You can take a picture also directly from the main road and they are worth stopping by all year round.
MONTALCINO
The fortress is standing virtually untouched today as it was never conquered – you can climb up the ramparts to enjoy some great views; in summer, the Jazz & Wine Festival takes place here.
A little down the hill is the Piazza del Popolo, Montalcino’s main (small) square, with a town hall (Palazzo dei Priori) adorned by a tall slender bell tower, the symbol of the town, and a shaded passage with the coats of arms of the different families once ruling the town. The streets in Montalcino are (even in the Tuscan context) quite steep. This makes the walking more strenuous, but at the same time the views plentiful. If you need to walk off your wine-tasting or a full Italian meal, wander into the side streets, like the Via delle Scuole, Via Spagni, Via Donnoli or Via Cialdini.
As most places around, Montalcino was founded by Etruscan, thrived during the 13-16th centuries, played a role in the Siena-Florence conflict and declined after Florence defeated Siena in 1559.
The most imposing structure in Montalcino is the pentagonal Fortress – built in 1361 on top of the hill after the Sienese snatched Montalcino from Florence. Its relations with Siena were so good that in 1555 it gave refuge to 700 Sienese families, who refused to submit to the Medici when Florence defeated Siena, and it became the “Republic of Siena at Montalcino”. The city’s loyalty is honored to this day at the Palio of Siena where their standard-bearer rides at the parade.
Now, back to #1 sight: the Brunello di Montalcino, one of the world's best and most appreciated Italian wines. Montalcino was already well-known for its fine red wines during the 15th century.
However, the precious formula of the fantastic Brunello was invented in 1888 by Ferruccio Biondi Santi, who first had the idea of leaving out the grapes used in the traditional Chianti recipe (Chianti wines require only 85% Sangiovese and permit a blend of other types of grapes) and using only the Sangiovese variety.
Before the Brunello is ready, it must age for a minimum of 5 years (6 years for a “riserva”), two of which must take place in oak barrels. However, the wine actually is best after some 10 years with ageing potential of a few decades for the best Brunellos.
If you want to taste it, there are couple of enotecas in the city center, which offer large selection of wines to taste, including some small refreshment. Our favourite is Enoteca di Piazza on Via G. Matteotti with more than 50 brunellos to taste at any time. For larger purchases, we typically go to the Enoteca Bruno Dalmazio just out of the old town, close to the lower parking. Another pleasant option is go directly to the wineries - our favourites include Tricerchi, Canalicchio di Sopra, Lisini, Ciacci Piccolomini, Baricci or Terre Nere
RADICOFANI
Radicofani is the fortress (with a village underneath) that you see from Chiancianello on the south horizon - the profile may remind you of a famous drawing from The Little Prince. It is worth visiting, especially if you want to absorb medevial atmosphere - already mentioned in Bocaccio’s Decameron - without the crowds. For now!
The medevial village of Radicofani is mostly just a main street Via Roma. You can start with an excellent coffee at the Bar La Stella at its lower gate, continue until you reach the Chiesa di Santa Maria Assunta, get lost for a few minutes in the little streets around Piazzetta del Teatro. There are some authentic, non touristy shops but aglione garlic is presumably the best in the region. If you have not noticed, the village is unique from the other hilltop places in Val d’Orcia - it is almost completely built from black lava rocks.
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Close to the Chiesa di Santa Agata, take a covered tiny street to the right, which will lead you to the climb towards the fortress (it’s a steep, unpaved path, the climb takes about 20 minutes). Alternatively, you can drive up to the fortress by car. The fortress is a must see on a sunny day, the views from its tower are truly breathtaking. And there is unpretentious restaurant with a fantastic grilled meat.
For centuries, the massive fortress was an important point on the Via Francigena and helped control the border between the Grand Duchy of Tuscany and the Papal State. It was also home to Ghino di Tacco, the Robin Hood of Val d’Orcia.
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Leaving Radicofani in the direction of Pienza, take the road through the village of Contignano. For us it is one of the most scenic drives you will be driving on the edge between 2 valleys with amazing views and deep ravines underneath you. Pavel highly recommends to try it on the bike, it is about 35 km roundtrip from Chiancianello.
Ghino di Tacco was an outlaw and a popular hero in 13th century Italy. He was born close to Sinalunga as the son of a Ghibelline nobleman.
Along with his father and brother Turino, he made a career of robbery and plunder while being hunted by the Sienese Republic. After they were caught, his father was executed in Siena’s Piazza del Campo, while Ghino managed to escape and sought refuge in Radicofani.
There Ghino continued his career as a bandit, but in the manner of a gentleman, always leaving his victims with something to live on. Boccaccio depicts him as a good brigand (Brigante buono) in the Decameron.
ROCCA & CASTIGLIONE D'ORCIA
Under preparation
