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Val d'Orcia from Montichiello
From Val di Chiana to Val d'Orcia: Montepulciano, Pienza and San Quirico d'Orcia by (e) bike

A three day tour in the Siena countryside

If you are planning a holiday in the Tuscan countryside, the Sienese area is definitely one of the best choices. Not far from Siena city centre is the Val d’Orcia, a hilly rural landscape included in the UNESCO heritage site list. Going east you’ll find the Val di Chiana, a vast fertile plain dominated by villages and towns of Etruscan origin and surrounded by medieval walls. 

From Montepulciano to San Quirico d’Orcia, this three day tour will take you through art towns, gravel roads, iconic landscapes and famous film locations.

Day 1

From the top of the tower to the underground cellars

Known as the capital of Vino Nobile, Montepulciano is distinguished by its 16th century architecture within a typically medieval urban structure. One of the best ways to explore the city is to walk along the main road (Corso) that crosses the town from Porta al Prato to Santa Maria dei Servi.

Make a stop in Piazza Grande, home to the impressive Palazzo Comunale. Its massive travertine façade conceived and carried out by the architect Mediceo Michelozzo resembles that of Florence’s Palazzo Vecchio. Climb the tower and you will have one of the best views of the Val di Chiana.

Climb down to the Piazza and go straight to the Civic Museum and Art Gallery Crociani. The Museum consists of around 180 paintings from the 16th - 17th centuries which were collected and donated to the city by the art collector Francesco Crociani. In addition, it hosts various Etruscan and Roman finds previously kept at the National Archaeological Museum of Florence.

Now is time to indulge in a wine tasting at one of the historic cellars. Montepulciano has a peculiarity: the Oldest cellars are located in the underground of the Renaissance palaces around the city. Walk along the many tunnels carved into the rock and taste the famous Vino Nobile di Montepulciano, defined by the poet Francesco Redi as the King of all wines.

Fun fact for vampire lovers: one of the main scenes of the Twilight saga (New Moon) when Bella saves Edward was shot in Piazza Grande at the entrance to the Palazzo Comunale.

Day 2

Riding to the capital of Pecorino

Start your day with a generous breakfast in a local bar. In Montepulciano you can visit one of the oldest cafes of Italy. Café Poliziano has been situated in the old town centre of Montepulciano since 1868. This large, elegant and distinguished Liberty-style coffee house was a cultural meeting point for writers like Carducci, Prezzolini and Pirandello.

If you feel energized after your cappuccino, get ready to ride your bike and visit Pienza! You can also rent an electric bicycle near Piazza Grande (you could check out Urban Bikery website partner of the Strada del Vino Nobile di Montepulciano wine route): the journey will be less tiring but just as exciting.

Leave Montepulciano and take the dirt road (Strada di S.Bartolomeo) that goes straight to the small town of Montichiello (halfway stop). Take a break and enjoy the view: Montichiello is a tiny fortified medieval village in the form of a castle and it’s known as the “Terrazza della Val d’Orcia” for its wonderful hilltop position.

Now travel along the road SP88 and then SP18 to Pienza. Ride, breathe deeply and fill your eyes and lungs with pure beauty.

Going to Pienza, you will cross the deviation to the road of Terrapille estate that was chosen by Ridley Scott for the final scene of The Gladiator, when Maximus comes back home just before his death.

Once in Pienza, walk along the main course and go straight to Piazza Pio II to visit the Duomo and the Piccolomini palace. Known as the ideal city and recognized since 1966 as a World Heritage Site by UNESCO, anyone visiting this city will have the feeling of being in a very special place. Explore its most romantic streets and don’t forget to taste the famous Pecorino cheese.

Day 3

Take in the sights of San Quirico d'Orcia

Leave Montepulciano and take the road SP146 to San Quirico d'Orcia. After about 20 kms you will find one of the most famous chapels of Tuscany. The Vitaleta chapel, probably of late Renaissance origin, lies within a private property, but you can take great pictures from one of the panoramic viewpoints along the road. Until 1870 it hosted a statue of the Madonna attributed to Andrea della Robbia, now on display at the homonymous Vitaleta church (Chiesa di Vitaleta) located inside the village.

Walking along the main street of San Quirico d’Orcia you will come across the Collegiata, a striking 12th-century church built on travertine and sandstone. It holds an organ dating from the 17th century, which, after a restoration, was revealed to have a great timbre.

Round off your tour with a visit to the Horti Leonini. Carried out by Diomede Leoni in 1580, it’s a superb example of the typical Italian garden conceived as a public space. It became property of the municipality of San Quirico d'Orcia in 1975 and today is regularly open to the public.

Many thanks to Strada del Vino Nobile di Montepulciano for inviting us to #IlBuonSecoloSenese blog tour. 
Read more about the tour (in Italian) here:

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