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Montepulciano hotels and flights

7 nights from

£271 per person

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Montepulciano is one of Tuscany’s most picturesque sights: a beautiful hilltop town surrounded by vineyards and olive groves. Situated close to Siena and less than an hour from Arezzo, the town is great for those seeking an authentic slice of Italy in a prime location. 

Inside of the historic walls, little construction has occurred since the Renaissance era, resulting in one of the most complete centro storicos in all of Italy. At the centre of things is the vast Piazza Grande, fronted by a magnificent town hall that mimics the hard lines and dramatic design of Florence’s Palazzo Vecchio. The stunning Tempio di san Biagio is just a short walk outside of the town’s medieval walls and remains a remarkable sight, with a gleaming dome that can be seen for miles and a grand interior adorned with frescoes. 

Food options are generally authentic, with numerous trattorie offering classic Tuscan dishes like bistecca alla Fiorentina (Florentine steak) and lamb ragu, often accompanied by a choice of excellent wines sourced from the vineyards of the region. For true vino connoisseurs, a number of local wineries and vineyards offer tours and tasting sessions.

Things to do in Montepulciano

The greatest hits of Montepulciano are easy to find – they huddle in the town centre. Just duck through an arch in the medieval wall and trace the gold-hued streets to the Grand Piazza. From there, you can climb the bell tower of the hulking Palazzo Comunale or admire the unfinished Montepulciano Cathedral.

Need a breather? Grab a table at the Gattavecchi Winery. Tuck into wild boar ragù, sip a glass of Montepulciano red, or peer into their 13th-century cellar. Alternatively, browse the shops dotting the surrounding roads. Souvenir stalls sit side-by-side with centuries-old bootmakers.

There is a reason to venture beyond the walls of Montepulciano – San Biago. You’ll find this grandly domed sandstone church at the end of a perfectly picturesque avenue of cypress trees.

Leaning Tower of Pisa

STATUE / MONUMENT / LANDMARK

Wine Tasting

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Excursions in and around Montepulciano

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