Our Top 5 Tuscan Hilltop Towns


Perhaps some of the most iconic images of Italy are of those picturesque shots of medieval towns perched atop the rolling, cypress-studded hills of Tuscany. But with such an incredible wealth of history and beauty in this one region, where do you look to visit first?

Having spent several summers living and travelling around Tuscany, I’ve put together a list of my 5 favourite Tuscan Hilltop Towns.


This virtually unknown little gem in Northern Tuscany holds a special place in my heart as the first place I ever stayed in Italy, in an old crumbling villa with an enormous veranda overlooking the town. It is a fantastic place to experience the rural tradition of “Sagra”, communal celebrations where everyone cooks and dines in the open air, often in the town’s main piazza with live music and a focus on a particular local delicacy. Barga in recent years has been the recipient of the Italian Touring Club’s Orange Flag in recognition of its beauty and excellence in tourism and environmental efforts, and featured in a BBC documentary about its unusual Scottish connections.

San Gimignano

Immortalised in countless art works, literature and cinema, the “city of beautiful towers” will always be one of my favourites. Despite the invasion of mass tourism in recent decades, there is still something magical about seeing those 14 medieval towers vying to stand tallest, rising from the golden countryside. Originally an Etruscan village, San Gimignano has a long and rich history, cemented in stone with the rash of tower building by lords eager to show off their wealth and power culminating in 72 medieval skyscrapers. Avoid the overstocked souvenir shops and you will find it well worth visiting the remaining “torre”, some of which you can still climb. My favourite thing to do in San Gimignano is to order a gelato from the award winning Gelateria di Piazza on the Piazza della Cisterna (try their chilli chocolate or blackberry and lavender!) and enjoy the views from a sunny spot.

Pienza View Poster


Moving south, we come to the first town on the list to feature in our food and wine tour of Tuscany. A UNESCO World Heritage Site in the middle of a UNESCO World Cultural Landscape, the Val D’Orcia, Pienza represents the ideal Renaissance town. Originally the village of Corsignano, Pienza was rebuilt entirely as the first example of humanist urban planning by the Renaissance Humanist Pope Pius II, born here as Aeneus Silvius Piccolomini in 1405, intended as a retreat from Rome. Nowadays the town is renowned by foodies for its cheese, Pecorino di Pienza, and enticing delis line the cobbled streets.


Our base for the Tuscan food and wine tours, this charming little town epitomises Tuscany for me; the sun kissed stone of Medieval and Renaissance architecture, the lively local restaurants serving the most local produce possible, and the gentle buzz of conversation as the town sun themselves outside the bars of the main piazza. Some of Italy’s most ancient human settlements have been discovered at Mount Cetona and this tiny town has its own Museum of Prehistory and Natural Archeology, and history is present everywhere, from the cave-like showrooms of ceramics hiding behind shop fronts to the gastronomic delights of Osteria del Merlo in the dungeon-like base of the old keep tower.


Perhaps the most iconic of Tuscany’s hilltop towns, ancient Siena reigns majestically from three hills, concentric circles of shaded streets winding their way up to the sundrenched Piazza del Campo. Shaped like a shell and sloping down to the rose-tinted Palazzo Pubblico and it’s Torre del Mangia, this wide, open arena forms the perfect stage for the city’s famous Palio. A traditional medieval horse race run twice each summer, representatives of the seventeen “contrade” (the city neighbourhoods created as battalions for the city’s defence) vie for a trophy banner or Palio. For a modern taste of Italian Medieval tradition, few places can match the electric atmosphere and age-old spectacle of Siena’s Palio.

Siena- Tuscany 2012

Categories: Festivals, Food, Foodie, Tuscany

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