First slide

Tuscany Tour in Pienza and Montepulciano

Private tour visiting Pienza and Montepulciano with private limousine service and English speaking driver.


Sightseeing daytrip in Tuscany to Pienza and Montepulciano with private transportation with chauffeured sedan and minivan from Siena, Florence, Montalcino, Cortona, Pienza and Montepulciano area, Arezzo, San Gimignano, Chianti, Perugia, Assisi, Orvieto, Todi and from all Tuscany and Umbria.




  • Private daytrip in Pienza and Montepulciano from Tuscany with private English speaking driver and transportation
  • Scenic itinerary through the iconic Tuscan landscapes of the Val d’Orcia
  • Learn all about the history of Pienza and view the beautiful art and architecture
  • The best of Montepulciano, with the charming renaissance squares and the amazing views of Tuscany
  • Behind the scene: Nobile di Montepulciano wine and Pecorino cheese in Pienza





Beautiful Tuscan views, excellent wines and cheeses, two lovely hill towns: all of this in a enchanting private tour in the heart of Tuscany with a private English speaking driver visiting Pienza and Montepulciano.


The Tuscany tour starts in Pienza, a jewel of the Renaissance protected by UNESCOwhich stands high upon a hill and overlooks all Val d’Orcia valley with amazing views. Birthplace of Pope Pius II (XVth Century), it was the same pope, under the influence of the new Renaissance style, who wanted to rebuild the whole town and try to make the “ideal city”. It is now considered one of the best example of the architecture of the XVth century and one of the most beautiful Tuscan hill town with its fascinating streets and charming Tuscan atmosphere.


Pienza is also famous for the production of Pecorino cheese so lunch stop con be arranged in a local cheese maker farm with a cheese tasting session and as well as lunch with a typical Tuscan menu, giving you the opportunity to taste the local products and the authentic Tuscan cuisine.


After a quick stop in the small village of Monticchiello for one of the most beautiful view of the Val d’Orcia, and driving on scenic roads through fields of sunflowers, vineyards and the gentle rolling hills, the tour in Tuscany moves to the gorgeous Tuscan hill town of Montepulciano. Rich of monuments of the Middle Ages and the Renaissance, Montepulciano is a delightful town, full of charm, where also one of the best Tuscan wines is produced: the Montepulciano Nobile DOCG wine and you should definitely not miss the chance to taste it visiting one of the many old historical wineries in the Montepulciano underground with their ancient atmosphere and wine tradition.

Departure available from:

  • The private tour in Tuscany visiting Pienza and Montepulciano is a private tour available from all Tuscany, Siena, Florence, Cortona, Montepulciano, Montalcino, Pienza, San Gimignano, Chianti (Radda, Gaiole, Greve, Castellina), Arezzo, Perugia, Assisi, Orvieto, Todi, Spoleto, Spello, Gubbio and from all Umbria and Italy.



  • approximately 8 hours



  • Qualified and professional English speaking driver
  • Luxury vehicle (Mercedes-Benz or equivalent)
  • Head office assistance and insurance coverage
  • Complimentary water
  • Wi-Fi on board
  • Local tour guide for walking tours (on request)
  • Traditional Tuscan lunch and cheese tasting (on request)
  • Winery visit and wine tasting (on request)

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.

Don’t miss! 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 Nobile of Montepulciano DOCG wine. 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.

Do not miss! Piazza Grande, Cathedral, Palazzo del Municipio, Gattavecchi Winery, Redi Winery

Get Tours recommends

Guided day tour in Tuscany with private car service and driver for visiting Montepulciano, Pienza, Montalcino and Val d’Orcia.
Tuscany day tour visiting Siena and San Gimignano with private limousine service and English speaking driver from all Tuscany.
Sightseeing day tour of Florence with private limousine service and English speaking driver available from all Tuscany, Umbria and Italy.
Wine tour in Montepulciano and Montalcino wine countries; guided wine tasting experience in Tuscany with private driver and wine expert.
Guided food & wine tour in Chianti, the heart of Tuscany, with private driver. Scenic itinerary through the Chianti wine region with wineries visits and wine, cheese and olive oil tastings.