First slide

Tuscany Tour in Montepulciano, Pienza and Montalcino

Daytrip in Montepulciano, Pienza, Montalcino and Val d’Orcia with private limousine service and English speaking driver.


Tour in Tuscany visiting Montepulciano, Pienza, Montalcino with private transportation from Siena, Florence, Cortona, San Gimignano, Chianti, Arezzo, Perugia, Assisi, Orvieto, Val d’Orcia, and from all Tuscany, Umbria and Italy.




  • Private daytrip in Montepulciano, Pienza and Montalcino from Tuscany with private English speaking driver and transportation
  • Scenic itinerary through the iconic landscapes of the Val d’Orcia
  • Learn all about the history of Pienza, Montepulciano and Montalcino and view the beautiful art and architecture
  • The best of these Tuscan hill towns strolling their charming streets and squares and enjoying amazing views of Tuscany
  • Behind the scene: Montepulciano and Montalcino, some of the best wine regions in Tuscany and the Pecorino cheese in Pienza





guided day tour with private limousine service and driver visiting the heart of Tuscany and exploring the enchanting Val D’Orcia and the charming Tuscan hill towns of Montepulciano, Pienza and Montalcino. 


The tour in Tuscany starts with Montalcino and from its fortress where you can enjoy the beautiful view and landscape of the Val D’Orcia and where it will be possible a wine tasting session of the famous Brunello di Montalcino DOCG wine. In fact, for all wine lovers the tour can include a stop in one of the best wineries of Montalcino for a private visit and a wine tasting session, and possibly a lunch with a typical Tuscan menu.


Leaving Montalcino, you will travel along a road which is one of the most beautiful and evocative of the whole of Tuscany: gentle rolling hills, picturesque olive groves, scenic country roads winding through perfect vineyards and isolated cypress trees atop hills.


The Tuscany tour continues in Pienza, a jewel of the Renaissance protected by UNESCO, which stands high upon a hill and overlooks all the Orcia valley with amazing views. Pienza is also famous for the production of Pecorino cheese and it will be also possible to taste it with a cheese tasting session.


The other stop on this private Tuscany tour is Montepulciano. Rich of monuments of the Middle Ages and the Renaissance, Montepulciano is a delightful town, full of charm, where another Tuscan top wine is produced: the Montepulciano Nobile DOCG wine. You should definitely not miss the chance to taste it visiting one of the many historical wineries in Montepulciano underground with their ancient atmosphere and wine tradition.

Departure available from:

  • The day trip in Tuscany visiting Montepulciano, Pienza and Montalcino 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 wine tasting (on request)
  • Wineries visits and wine tastings (on request)
  • Pecorino cheese tasting (on request)

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.

Do not miss! Sant’Antimo Abbey, Fortress, Val d’Orcia National Park.

Called Corsignano until the XVth 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.

Do not miss! Cathedral, Palazzo Papale, 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

Val D’Orcia:
It is a valley in the south of Tuscany taking its name from the river Orcia which flows through its center. 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.

Do not miss! Scenic route on road numbers SS2 and SS146, Cypress Woods in San Quirico d’Orcia, Chapel of Vitaleta.

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.