Siena & Val d'Orcia is Tuscany at its most concentrated: a UNESCO-listed medieval city with a piazza that doubles as a racetrack surrounded by the most photographed countryside on the continent.
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Nowhere feels more quintessentially Tuscan than the Val d’Orcia. A UNESCO World Heritage Site, the valley is an almost impossibly perfect scene of wheat fields, vineyards and scattered Renaissance towns, each more beautiful than the last: Montalcino and its Brunello estates and fortress views; Montepulciano and its barrels of Vino Nobile; and Pienza, designed in the 15th century as the “ideal city” and still known for its pecorino cheese, best tasted warm and freshly cut. The largest of the towns is ochre-hued Siena, one of the most finely-preserved medieval cities in Italy and divided into seventeen neighbourhoods or ‘contrade,’ each with its own coat of arms and traditions, making every wander a foray into a new world.
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In Siena, start your wanderings in the Piazza del Campo, the shell-shaped square where the famous Palio tears around the cobbles each summer, then climb to the marble-striped Duomo to gaze at Pinturicchio's frescoes in the Piccolomini Library. Pair your sightseeing with a cooking class in Contessa Piccolomini's 11th-century palazzo and you've got a perfect day in town. Head south and the Val d'Orcia unfolds like something out of a fairytale – that stretch of cypress-lined ridges and ochre hill towns that looks as if it fell straight from a postcard. Amble through Pienza, the Renaissance ‘ideal city’, and watch fresh pecorino come together with a local cheesemaker, before tasting the grapes. Brunello in Montalcino and Vino Nobile in Montepulciano are not to be missed. For a completely different view, take to the skies and see the valley in all its glory on a sunrise hot air balloon flight, or take it slow on a Vespa or bicycle along the back roads.
Siena encapsulates the romance of the Italian middle ages and keeps traditions alive, especially during the famed Palio horse race - a thrilling event that takes over the entire city.
Beyond Siena's most well-known sites, take the time to explore the quieter corners. Enjoy a leisurely stroll through the Botanical Gardens or around the walls of Fortezza Medicea for an unrivalled view of the city.
Siena is easy to explore on foot and there's limited car access in many areas. Be mindful that it's a hilly city with many steep streets and staircases, so comfortable shoes are a must.
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