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Pienza and Montepulciano Tour

Private Tour of Montepulciano and Pienza with private English speaking driver and car, minivan, minibus for hire

Beautiful views, excellent wines and two adorable antique hamlets: all of this in a enchanting private tour in the heart of Tuscany. The first stop of the tour is Pienza, a true jewel of the Renaissance, recognised as a protected site by UNESCO. Birthplace of Pope Pius II (XVth Century), it was the same pope, under the influence of the new Renaissance rules, who wanted to rebuild the whole town and try to make the “ideal city”. Pienza is also famous for the production of Pecorino cheese so the visit ends with a stroll through the streets and squares of the town, where you will find many distinctive cheese shops and delicious craft shops. The other stop on the tour is Montepulciano which is reached by scenic roads through fields of sunflowers, vineyards and sweet hills. With a historical centre which shows indelible signs of the Middle Ages and the Renaissance, Montepulciano is a delightful town, full of charm, where one of the best wines of Tuscany and Italy is produced: Montepulciano Nobile DOCG wine, which you should definitely not miss the chance to taste in one of the many wine shops in the town.


Duration: approximately 7 hours

Included: comfortable air conditioned vehicle, private driver (English speaking) at your disposal for duration of tour, taxes, fuel, parking, motorway tolls, meal of the driver, and of “our best”!

Not included: lunch, entrance fees to monuments or museums, wine tasting, and anything not specified as “Included”.

It is possible for the tour to leave from locations in Tuscany and Umbria, within the areas in which we operate (click here to view map) and, based on logistics, the specific programme can be modified.



Pienza: Called Corsignano until the XV th Century, when, Pope Pius II, originating from here, ordered the famous Renaissance architect, Bernardo Rossellino, to completely reconstruct the town, following the new Renaissance  aesthetics. Pienza, named in honour of its most famous son, is considered the “ideal city” for its urban design. In 1996 it was added, together with the Val D'Orcia to which it faces, to World Heritage sites, protected by UNESCO. It should also be remembered for the production of Pecorino of Pienza, a hard cheese made from sheep's milk.

Cathedral, Palazzo Borgia, Palazzo del Comune, Palazzo Piccolomini

Of Etruscan origin (IV-III BC), the city knows the real phase of splendor during the medieval and renaissance period, marked by political prestige, flourishing economy and cultural value. Coveted by Florence and Siena, it grows and develops in the municipal period, until 1390, the year in which it passed under the control of Florence, where Montepulciano represented a territorial outpost in the area of Siena. The growth continues in the Renaissance, giving illustrious names to the church, the arts, letters and to politics of that period.

The city is also famous for the richness and excellence of its vineyards, from which is produced the Vino Nobile of Montepulciano DOCG. It is one of the oldest Italian wines (testimonies from 783) and is characterized by Sangiovese and Canaiolo grapes, with a minimum aging process of 2-3 years.

Piazza Grande, Cathedral, Palazzo del Municipio, Gattavecchi Winery, Redi Winery