From the top of the tower to the underground cellars
As a base you can choose Montepulciano which works well because it lies between two valleys: Val d’Orcia and Val di Chiana. 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.
Now 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.
Until September 30 the Museo Civico will host the Finest Century of Sienese art exhibition, showcasing some masterpieces of the Sienese school from the XVI and XVII centuries. The exhibit takes place across another two towns you will be visiting next: Pienza and San Quirico d’Orcia. But before you go, 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.
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, 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. Walk along its most romantic streets and don’t forget to taste the famous Pecorino cheese.
At Conservatory San Carlo Borromeo you can visit the second section of the exhibit “Finest Century of Sienese art exhibition” dedicated to Rustichino and admire his Caravaggesque style.
San Quirico d'Orcia
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.
Just in front of the church, you can visit Palazzo Chigi Zondadari and the last part of the exhibit The Finest century of Sienese art showcasing the monumental Virgin and Child by Bartolomeo Neroni, known as Riccio.
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 private garden reserved for a few, 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:
Other Time-based tours
- flag Sporty More demanding itineraries for highly trained cyclists and those who love a challenge, with the toughest climbs and hardest roads
- nature Scenic bike itineraries In the loveliest of places, immersed in nature, by the sea and through historical old towns
- location_city Urban itineraries Fascinating bike tours around the artistic treasures of Tuscany's major towns and cities
- wc Bike itineraries for tourists and for families Easy itineraries along the coast, in the hills and towns, suitable for families with children