Pienza and Montepulciano Area

“A must for star-crossed lovers and wine aficionados.” - Reviewed by Deborah

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The landscape that surrounds the picturesque towns of Pienza and Montepulciano as well as San Quirico d’Orcia and Montalcino, is some of the most emblematic countryside you will see in Tuscany. It’s the stuff that postcards are made of and that artists drool over – scenic photo opportunities abound here. Yes, we mean saluting cypress trees, combed vineyards, rolls of haystacks on golden fields, medieval hilltop settlements, olive groves, ancient churches and stunning villas.

Such is the beauty of the Val d’Orcia which essentially unites these two destinations – an iconic valley that it is protected as a UNESCO World Heritage Site. Choosing to stay in any part of this region is an absolute visual treat – plus you will be a short drive from some of Tuscany’s most distinguished wine destinations: Montepulciano (Vino Nobile) and Montalcino (Brunello).


Pienza is the perfect example of Renaissance town-planning at its best and most efficient. The once medieval hamlet was turned into a breathtaking example of Renaissance architecture by architect Bernardo Rossellino upon the orders of Eneas Silvio Piccolomini – better known as Pope Pius II – who was born in Pienza in 1405. The Pope also changed the town’s name from Corsignano to its present-day title.

You can easily navigate Pienza in less than half an hour to get a general taste, and you will find it impeccably clean and friendly. Highlights include the town’s main monuments on the Piazza Pio II, such as the cathedral tower and the Palazzo Piccolomini. Foodies can treat themselves to some fabulous restaurants, great gelato and wander through fabulous shops where the star product is Pecorino cheese (a Tuscan delicacy made from local sheep’s milk).

Movie and literary buffs will love that Pienza was the set for various scenes in Franco Zeffirelli’s 1968 movie adaptation of Shakespeare’s Romeo and Juliet. The town was also featured in Anthony Minghella’s 1996 film, The English Patient and Ridley Scott’s 2000 epic, Gladiator.


Take the S146 road east of Pienza about 6km (4 miles) and you will arrive to Montepulciano, located on a narrow limestone hilltop more than 600 meters high and famous for its Nobile de Montepulciano wine. Be prepared to exercise your calf muscles; part of this town’s uniqueness comes from its steep inclines.

Besides trying a glass or two of its celebrated wine in any of the various wineries in town or organizing a full-on vineyard tour, another highlight is to take a stroll around the Piazza Grande and visit the Palazzo Tarugi. To get there, you will inevitably have to climb the corso, a steep street full of restaurants, wineries and shops. Likewise, you might enjoy the Gothic façade of the Palazzo Comunale or want to visit some of the many churches, including the famed Church of the Madonna di San Biagio.


  • Tuscany, central Italy
  • 2 hrs to Florence International Airport
  • 2 hrs 30 mins to Rome International Airport
  • 1 hr to Siena
  • 1 hr to Arezzo


  • Wine Tastings – You will be spoiled for choice for wine tasting tours, with options for days tours and even wine classes in Montepulciano and Montalcino in particular. We can even organize custom wine tastings – tell us your favourite Brunello vintners and we’ll organize custom vineyard tours and tastings with lunches and special vintages where possible.
  • Sightseeing – Day trips to Florence, Siena, Arezzo, Montalcino and San Quirico de Orcia.
  • Hiking and Cycling – This is a fabulous region for cycling and hiking.
  • Gastronomy – Discover the many local and regional dishes with plenty of restaurants to suit every taste and budget.
  • Cooking Classes – Learn how to cook authentic Tuscan recipes from expert native chefs.
  • Hot Springs – Enjoy natural thermal baths in this area.
  • Movie Hunting – Visit scenery made famous by popular movies such as Under the Tuscan Sun, The English Patient, Gladiator, Life is Beautiful and Romeo and Juliet.