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8 Days in Montepulciano

By Dom Gagliardo

While traveling through Italy several years ago, I discovered the large town of Montepuliciano, where I wine tasted and then roamed the narrow cobblestone streets of this wonderful gem in Tuscany. I was so mesmerized and enthralled with its charm and history I realized one day was not enough and vowed to return for a much longer stay, and that is just what I did two years later.

            Situated in the heart of Tuscany, approximately halfway between Florence and Rome, this medieval hilltop town dates back to the Etruscan Era from over 2000 years ago. However, its most visible historic presence dates back to the 12th century, with indications of the alternating power struggle between the local royal families from Siena and Florence. Everywhere you look, there are reminders of the competing influences of these powerful families.

            Once protected from Barbaric invaders by the wall that still surrounds the town, its four portals (gates) that kept out unwanted enemies now remain open, welcoming everyone to see and enjoy this bustling community with its collage of Renaissance architectural styles. Take a walk along the Corso that rises from the main portal and meanders its way up a steep hill to the famed Piazza Grande that exudes a dominant Florentine influence. This town square is flanked on all sides with four beautiful palazzos, the most prominent being the Palazzo Contucci, built in the 16th century and still home to family members, and the Contucci Cantina, whose basement chambers have been filled with barrels of wine since the 1500s. Along the way, stop in any number of palazzos, such as the DeRicci Cantine or Cantina della Tolosa, for a taste of the noteworthy and namesake wine, Vino Nobile di Montepuliciano.

            As formidable as the palazzos are, one cannot overlook the churches peppered throughout the town, such as the Church of San Francisco and the Duomo. But the most impressive of all is San Biagio Church, located outside the wall at the base of Montepulciano’s hill. A cypress-lined driveway leads up to this Renaissance style church built from local travertine in the mid-1500s.

            Travelers from the US planning to visit Tuscany will generally fly into Rome or Florence. While there are currently great fluctuations in airfares, a recent survey revealed that round-trip economy fares to both cities start at approximately $1600, including seat assignment and baggage fees. Montepulciano is easily accessible by train from both of these cities and while I never recommend renting a car in those cities, having your own vehicle in Tuscany will truly enhance your experience. In addition, the roads are extremely manageable while you day trip to sightsee or enjoy wine tasting in other cities and towns like Siena, Pienza, Montalcino, Orvieto, and Chianti, to name a few.          

            While standard hotel lodging may seem somewhat limited, there are many options for all budgets through VRBO or Airbnb. For example, I located a five-room apartment in an old villa situated right on the wall for only $125 per night. The views from the patio and garden of the surrounding valleys were inspirational, but more importantly, living among the locals provided an opportunity to appreciate and understand the cultural aspects of the town.

            And then, of course, there is the Tuscan fare—from the freshest of pastas and olive oils to the Pecorino Romano cheese. Montepulciano is dotted with wonderful cafes, bistros, and restaurants. Begin your day with a cappuccino and a cornetto (croissant) at the Caffe Polizano, a popular meeting place since 1868. With so many dining choices, like LaVineria di Montepulciano, Osteria del Conte, or Le Pentolaccia, decisions about meals are often tastefully difficult. But for the carnivores out there, I highly recommend Osteria dell’Aquacheta, where guests can gaze at the open fire oven and slabs of fresh beef lying on the counter until Guilio, the owner, brings cuts of meat to your table from which to choose to prepare the most delicious Florentine steak you will ever devour.          

            Whether it’s exploring the narrow streets of this majestic town, driving around the verdant fields and vineyards of Tuscany, or getting your fill of gastronomic delicacies and vino, vino, vino, it will leave you wanting for more. For that reason, I plan to return very soon. Ciao!

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