Cortona occupies one of the most spectacular positions in all of Tuscany. Perched on a steep hillside above the Val di Chiana, with Lake Trasimeno visible on clear days shimmering in the distance to the south-east, the city commands views that stretch from Umbria to Arezzo and beyond. Its Etruscan origins give it a depth of history that predates most of Tuscany’s famous medieval cities by many centuries, and its streets of steep stone staircases and terracotta-roofed houses rising in tiers above the valley have made it one of the most visited hill towns in central Italy. For guests at Villa Talciona, Cortona is approximately 90 kilometres to the south-east, roughly an hour’s drive, which makes it a full but very worthwhile day trip.
The Setting and How to Arrive
The drive to Cortona from Poggibonsi follows the A1 motorway south to the Val di Chiana exit, then a straightforward road to the base of Cortona’s hill. From there, the town itself climbs steeply: most visitors park in one of the car parks at the lower levels (near Piazza del Mercato) and either walk up through the town (15 to 20 minutes of steep climbing through beautiful streets) or take the shuttle bus that runs at intervals to the upper town. The effort of climbing is amply rewarded by the views that open up at every turn.
Cortona is in the Arezzo province of Tuscany, close to the Umbrian border, and this geographical position gives it a slightly different character from the Sienese towns that surround Villa Talciona. The landscape around it is broader, more open, and the light in the Val di Chiana has a particular quality that painters have been responding to for centuries.
Etruscan Academy Museum: Ancient History in an Unexpected Setting
The Museo dell’Accademia Etrusca e della Città di Cortona (MAEC) is one of the most rewarding museums in Tuscany and is frequently underestimated by visitors who do not know it. The Etruscan collections are exceptional: the centrepiece is a fifth-century BC bronze lamp, a circular chandelier of extraordinary intricacy and craftsmanship decorated with 16 oil lamps, Gorgon faces, and mythological figures. It is one of the finest Etruscan bronze objects in existence.
The museum also holds a significant collection of Egyptian antiquities (a legacy of eighteenth-century Cortonese scholars who were among the first to attempt serious decipherment of hieroglyphs), as well as Renaissance paintings, Roman finds, and a collection of works by the Futurist painter Gino Severini, who was born in Cortona. The combination is eclectic in the most engaging way.
Piazza della Repubblica and the Town’s Heart
Cortona’s main square, the Piazza della Repubblica, sits roughly in the middle of the hillside town and is the social hub of daily life. The Palazzo del Comune (town hall) with its external staircase and medieval tower gives the square its dignity without overwhelming it, and the surrounding streets are full of the independent shops, wine bars, and trattorias that characterise a functioning hill town rather than a tourist-only destination.
The adjacent Piazza Signorelli, named after the great Renaissance painter Luca Signorelli who was born in Cortona, is equally attractive and slightly quieter. Cortona’s streets invite walking without a fixed agenda: the staircases and alleys that connect the different levels of the town constantly open onto unexpected views of the valley below.
The Views: Lake Trasimeno and the Val di Chiana
The views from Cortona are among the finest in Tuscany. From the upper parts of the town and from the ruins of the Medici Fortezza (reached by a steep climb above the town, but rewarding for those with the energy), the panorama encompasses the broad agricultural plain of the Val di Chiana, the blue expanse of Lake Trasimeno on the Umbrian border, and on clear days, the profile of Monte Amiata to the south. In the summer haze the lake can take on an almost mirage-like quality.
The best views in the town itself are from the public gardens near the church of San Domenico and from the piazzale at the top of the main street. Both are accessible without climbing to the fortress and are excellent for photography.
Local Restaurants and Eating in Cortona
Cortona’s restaurants serve food that reflects its position at the confluence of Tuscan and Umbrian culinary traditions. The bistecca, the wild boar pasta, and the ribollita of Tuscany appear alongside Umbrian-influenced dishes using truffles (particularly black truffles from the surrounding hills), lentils, and fresh pasta shapes. The local DOC wine is Cortona DOC, which includes both Sangiovese and Syrah (Cortona has become particularly noted for its Syrah in recent years, a surprise in a region most associated with indigenous varieties).
For lunch, the trattorias on the smaller streets away from the main tourist circuit tend to offer better food and value than those directly on the main piazza. The local bruschetta with fresh olive oil from the surrounding groves is a simple pleasure that is available everywhere.
Frances Mayes and “Under the Tuscan Sun”
For many visitors, especially those from the English-speaking world, Cortona carries an additional layer of association with Frances Mayes, the American writer whose memoir “Under the Tuscan Sun” (1996) described her purchase and restoration of a farmhouse called Bramasole near Cortona and her gradual immersion in Tuscan life. The book, and the film adaptation starring Diane Lane, introduced a generation of readers to the specific pleasures of rural Tuscan living and contributed significantly to the international popularity of Cortona as a destination.
Bramasole itself is a private property on the lower slopes of the hill below the town and can be seen from the road (it is signposted), though it cannot be visited. The book’s descriptions of markets, olive harvests, and the rhythms of life in the Val di Chiana remain evocative reading before or after a visit to the town.
Terracotta Crafts and Shopping
Cortona has a tradition of terracotta craft production, and the town’s artisan shops sell a range of locally made ceramics alongside the usual range of Tuscan food products: olive oil, wine, truffles, and dried pasta. The quality of the ceramics varies considerably: the best pieces are handmade to traditional designs in local workshops, while cheaper tourist goods are produced elsewhere. Taking time to look for a craftsman’s mark or to ask about provenance is worthwhile.
For guests at Villa Talciona, Cortona represents one of the longer day trips but one that combines art, history, extraordinary views, and good food in a way that is difficult to match. Explore all the day trip options from the villa to plan your full Chianti itinerary.
The combination of Etruscan depth, Renaissance beauty, cinematic fame, and landscapes that seem designed for contemplation makes Cortona a destination worth the drive from Talciona. Book your stay at Villa Talciona and make Cortona part of a week that covers the very best of Tuscany.
