VAL D’ORCIA IN FOCUS

Day trip to Montalcino, Pienza & Montepulciano from Siena

  • Step into a life-size canvas to admire the splendid landscape of Val d’Orcia and three of its best-loved towns
  • Rewind the clock to the olden days of lords and dames as you stroll through the medieval streets of Montalcino
  • Visit the model Renaissance town of Pienza, a perfect embodiment of humanist ideals and planning principles
  • Category
  • Hobbies & Interests
  • Duration
    9 hours
  • Destination

VAL D’ORCIA IN FOCUS

Day trip to Montalcino, Pienza & Montepulciano from Siena

Head for Tuscany’s picture perfect destinations in the comfort of your private chauffeured vehicle and get a close look at an entrancing triptych on this full-day trip to Val d’Orcia.

Lying south of Siena, the Orcia Valley, with its verdant plains, gently rolling hills, fortified villages and rural landscapes has inspired a whole school of painting – the refined Siennese School which blossomed between the 13th and 15th centuries – and still delights visitors today having retained its pure, unspoiled allure. Val d’Orcia was declared a UNESCO World Heritage Site in 2004 since it is “an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing picture”.

Breathtaking landscapes, enticing cuisine, top-class wine and finely preserved medieval and Renaissance towns make Val d’Orcia a must-see on your Tuscan exploration. Examine the brushstrokes and the brilliant palette of this life-size composition, as you ride through the glorious scenery.

The first stop on your excursion will bring you to Montalcino, internationally known as the capital of the Brunello wine region. This hilltop town has undergone few changes since the 1300s, when it was a stronghold belonging to the city of Siena. Protected by fortified walls, Montalcino has indeed maintained its medieval appearance and offers splendid views of the surrounding countryside from the top of its 14th century fortress: hills crossed by rustic lanes winding though vineyards and olive groves, a canvas splashed with golden sunflowers and deep green cypress trees. Enjoy a leisurely stroll through the town’s narrow alleys lined with wineries, craft shops and cafes and linger in the distinctive medieval aura of the quaint Piazza del Popolo before setting off for another of Val d’Orcia’s gems.

Time seems to have come to a standstill in Pienza. Conceived as a model city, this is the best-preserved Renaissance town in Tuscany. Pienza, meaning the city of Pius, was founded by Pope Pius II who wanted to transform his lacklustre place of birth into the ideal embodiment of Renaissance values. He commissioned architect Bernardo Rossellino with the task of building a town in accordance with humanist planning principles. The result is a harmonious 15th century urban centre which is still surprisingly intact. Make your way through the olde worlde streets to the small but perfectly proportioned Piazza Pio II, the heart of Pienza’s religious and political life for almost six hundred years. Here you will admire the Cathedral of Santa Maria Assunta and the elegant palazzi that together make up one of the finest corners of Tuscany. A walk along Via dell’Amore – Lovers’ street – and Via del Bacio – Kiss street – will make you fall head over heels for Pienza. You might also be interested to know that the town holds the title of the capital of pecorino. Before moving on, a stop to refuel with a lunch, including a sample of this flavoursome cheese, is highly recommended.

Standing proudly on top of a steep hill, Montepulciano still boasts a medieval and Renaissance urban fabric which has remained remarkably untouched since 1580. Rural, yet chic and romantic, Montepulciano is Tuscany’s pride and joy. A collection of sumptuous palazzi punctuates the town centre, proclaiming the importance of the site and the wealth of the local nobility during the 14th and 15th centuries, although it was not until the 1500s, under the rule of the Medici dynasty, that Montepulciano rejoiced in its golden age. Amble along the main Corso and reach Piazza Grande, the very core of the town. Here you will find the beautiful unfinished Duomo and the imposing Palazzo Comunale with its characteristic clock tower. Climb to the top for a sweeping view of Montepulciano and the surrounding countryside. The square is the setting for the folkloristic Bravio delle Botti, a wine barrel racing contest held every year in August that pays homage to Montepulciano’s most important trade. Indeed the history and fame of this small town are inextricably linked to its world-renowned Vino Nobile di Montepulciano, one of Italy’s oldest wines. To get a true taste of the town don’t forget to take a peek inside one of the atmospheric subterranean cantine, hidden beneath its buildings, and enjoy a glass of this full-bodied red wine.

Relax on the ride back to Siena after a richly satisfying day of discovery.

What is included in this experience?
  • A Mercedes vehicle and professional driver at your disposal for a full-day excursion to Montalcino, Pienza and Montepulciano from Siena (approx. 9 hours)
What is not included in this experience?
  • Tips
  • Meals
  • Entrance tickets to museums and sites
Additional information
  • This is an independent sightseeing experience – no guided tours have been included
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