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Montalcino, Pienza and Montepulciano Tour

Private Montalcino, Pienza, Montepulciano Tour with English Speaking Drivers

The tour starts with the Sant’Antimo Abbey, an ancient Benedictine monastery known for its Gregorian chants, and it continues to Montalcino, home of Brunello di Montalcino DOCG wine. From its fortress you can enjoy the beautiful landscape of the Val D’Orcia, while strolling through the town centre you will have the chance to have lunch on a terrace with a spectacular view. Leaving Montalcino, you will travel along a road which is one of the most beautiful and evocative of the whole of Tuscany, and includes a stop at 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. 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 8 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.



Montalcino: The name of the town has roots in the Latin words Mons (mount) and Ilex (holm oak), and holm oak is actually the symbol of the city. During the Middle Ages it experienced its heyday, thanks to its position along Via Francigena (imported road linking Canterbury, France, Rome and Jerusalem), and it is in this period that legend has it that the Emperor Charlemagne, travelling from Rome to France, wanted to found the Sant’Antimo Abbey. The town is also famous for its Brunello di Montalcino DOCG wine. The wine is one of the most important and appreciated worldwide, and involves only the use of Sangiovese Grosso grapes, with a minimum aging process of  5-6 years.

Sant’Antimo Abbey, Fortress, Val d’Orcia National Park.

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

Val D’Orcia:
It is a valley in the south of Tuscany taking its name from the river Orcia which flows through its centre.  Characterized by sweet hills and cypress trees, since 2004 is a national park, included among the sites protected by UNESCO as a World Heritage Site, because of its perfect blend of history, art and natural beauty. From the Renaissance to modern photography, it has always been a source of inspiration to artists and painters.

MISS!!! Scenic route on road numbers SS2 and SS146, Cypress Woods at San Quirico, Chapel of Our Lady Vitaleta.