Etruscan Cities

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Private Southern Tuscany Food and Wine Tour

Val D'Orcia - Landscape
Pienza - viewPienza - Piazza Papa PioIIPienza - Duomo - FacadePecorino di Pienza - SelectionPienza - WellMontepulciano- viewMontepulciano - PiazzaMontepulciano - SquareNobile Montepulciano

From: $179.42



8 Hours


08:00 AM

Mon,Tue, Wed, Thu, fri, sat, Sun


Pick-up at your hotel, more details at booking




Your private Southern Tuscany Food & Wine Tour will take you on a charming journey to discover the beautiful towns of Montepulciano and Pienza.

Your driver and guide will meet you at your accommodation in Rome to take you on a full day excursion.

The journey will start immediately while you enjoy the delightful views from the car. Leaving Rome you will head to the North and pass through the gorgeous countryside. In two hours you will reach your first destination: Montepulciano.

The medieval town of Montepulciano is located southeast of Siena on a hill. The city is famous not only for the beautiful historical center but also for the delicious food and wine.

The origins of Montepulciano are Etruscan. When the Romans took over the Etruscan possessions it became a garrison for road patrols. Later the Lombards turned the town into a religious center. During the Renaissance period many beautiful palaces were added to the city. The tour will take you to the wonderfully preserved historical center of the city. During your 90 minutes walk your private guide will showcase you the main sights of the city: the Palazzo Comunale, the town hall designed in the same style as Florence’s, Palazzo Tarugi, and the Cathedral of Santa Maria Assunta, also called the Duomo of Montepulciano.

After the city tour is the time to try the famous wine of Montepulciano! Visiting a historical winery you will taste three famous wines of the area: Rosso di Montepulciano (Red of Montepulciano), Vino Nobile (Noble Wine) and Vin Santo (Holy Wine). These incredible wines will be pared with a mouth-watering “tagliere” a selection of local charcuteries and cheeses.

Montepulciano’s wineries are very interesting. The historical ones have adapted Etruscan tombs into “cantine” (cellars). Those locales maintain the perfect climate all year round, not too cold during the winter and not too hot during the summer.

Now your driver and guide will bring you to visit the unique renaissance town of Pienza. Pope Pius II decided to have the entire village rebuilt as an ideal Renaissance one. Many Italian and European cities later adopted this model. UNESCO declared Pienza a World Heritage Site in 1996. The most important buildings of Pienza are located in the central Piazza PIo II. Your guide will show you the beautiful Palazzo Piccolomini, Palazzo Vescovile and the Duomo.

At the end of Pienza’s tour you will return to your accommodations in Rome.



– Round trip transportation with private car

– Expert English speaking driver coordinator

– Wine tasting and light lunch


– Visit of Montepulciano

– Visit of Pienza

– Visit of a Historical Winery

– Confirmation will be received at time of booking

– Voucher and detailed operator information, including local emergency numbers will be received three weeks before the date of your tour.

– Adult pricing applies to all travelers

Departure point:
Pick-up at your accommodation

8 hours

Return details:
Drop-off at your accommodation


Pitigliano - night view
Pitigliano - Jewish CemeteryPitigliano - Day ViewPitigliano - Palazzo Orsini

Pitigliano is located on a tuff’s cliff in southern Tuscany.

This was the center of the Etruscans civilization. Around the village it is possible to admire the cave-tombs built during their domination. Most of the caves are still in use as cellars and lockers.

The subsequent Roman domination on the other hand didn’t leave many signs; hidden in the cellars under some old houses there are niches that were used to keep the urns of the dead.

During the medieval period the city was ruled by three major aristocratic families: the Aldobrandeschi, the Orsini and the Medici.

For many centuries the city housed a very well integrated Jewish community.

Pitigliano’s location, at the border between the Papal State and the Gran Duchy of Tuscany caused many Jews here to find the peace that they couldn’t have under the Pope’s jurisdiction.  When the Reign of Italy was founded the Jews became citizens and many families started to leave the small village for bigger cities. When the Mussolini’s government passed the Racial Laws there were only a small Jewish community left in Pitigliano; all the Jews fled to avoid capture thanks to the help of their Christian fellow citizens.

Things to see

After the Second World War almost no Jews went back in Pitigliano; however the cultural heritage is very well preserved.  Entering the ancient Ghetto is possible to visit the 16th century synagogue, restored and reopened in 1995. Beneath the temple are located the areas used for the ritual bath, the kosher butcher and winery and the outstanding Forno delle Azzime (the old kosher bakery).

Also the Jewish cemetery survived the many changes that involved the community.

Walking through Via Zuccarelli and the alley Goito it is possible to reach the Old Mill Pelliccetti used by the Jewish community for many years.

Pitigliano is very famous for its wine; the Bianco di Pitigliano (White of Pitigliano) has won many awards. Lately also its kosher version is becoming very celebrated.