Golden hills, thermal steam rising at sunset and vineyards turning ruby-red: autumn in Tuscany creates a natural setting that seems to have stepped out of a painting.
At this time of year, villages and lesser-known small towns show a more authentic side, with museums, Renaissance squares and artisan workshops. Grape harvest and truffle season add solid reasons for a trip, bringing together food, scenery and history.
Cortona, the Etruscan hill town overlooking the Val di Chiana
Perched on a promontory close to the Umbrian border, Cortona has an urban layout that traces centuries of history, with ancient-origin walls and the medieval imprint of its centre.
Its two main squares, Piazza della Repubblica and Piazza del Duomo, frame landmarks including the Town Hall and the Cathedral of Santa Maria Assunta. Cobbled lanes and stone houses then lead towards unexpected viewpoints over the surrounding countryside.
The MAEC – Museum of the Etruscan Academy and the City of Cortona holds important archaeological finds and evidence from several eras. Meanwhile, the Diocesan Museum displays major works from the great period of religious art, including Fra Angelico’s celebrated Annunciation.
Asciano and the Crete Senesi, where the scenery changes with the seasons
In the rolling Crete Senesi area, Asciano is a compact medieval village surrounded by walls and clay fields that take on warm tones in autumn. A walk through the centre passes the Basilica of Sant’Agata, the Torre della Mencia and the Church of San Francesco, with glimpses of the town’s long history at every turn.
For cultural stops, there are two good options: the Civic Museum of Archaeology and Sacred Art, housed in Palazzo Corboli, and the Cassioli Museum, dedicated to 19th-century Sienese painting.
Paths lead out through the village gates and into the lunar-looking scenery of the Crete Senesi, well suited to an unhurried walk. In December, the town hosts a market exhibition devoted to white truffles, a tradition that reflects its close connection with local food.
Scansano, Maremma hills and the home of Morellino
In the heart of the Maremma, Scansano stretches across a hill surrounded by vineyards. Its name is immediately associated with Morellino di Scansano, the area’s signature wine, which also has a dedicated Museum of Vine and Wine inside Palazzo Pretorio.
The old walls, with their 15th-century tower and the Porta Grossetana, bear witness to the town’s history under the Aldobrandeschi, Sforza and Medici families. Nearby, three castles recall a strategic past: Montorgiali, Montepò, now restored, and the ruins of Castello di Cotone.
Pienza, the “ideal city” among hills and pecorino shops
At the heart of the Val d’Orcia, Pienza occupies a hilltop overlooking postcard-perfect scenery of gentle slopes and lines of cypress trees. Its historic centre, the result of a unified Renaissance project, is an urban masterpiece that has earned a place on the UNESCO World Heritage List.
The coherence of the original vision is easy to sense, with Piazza Pio II at its centre, surrounded by the balanced proportions of Palazzo Piccolomini, the Cathedral, Palazzo dei Canonici, the Town Hall and Palazzo Ammannati.
Autumn also brings enticing aromas to the village shops, where cheeses and artisan pecorino reflect a deeply rooted local craft. Between stops, the lanes lead to natural terraces overlooking the Val d’Orcia.
Volterra, Etruscan roots and stone-built elegance
Volterra’s Etruscan past is visible as soon as you reach Porta all’Arco, with its celebrated carved heads that hark back to antiquity. Outside the medieval walls, the Roman amphitheatre, dating back to the imperial period, is one of the peninsula’s most evocative archaeological sites.
The village centre revolves around the striking Piazza dei Priori, dominated by austere stone palaces that reveal the city’s long civic history.
The nearby Palazzo Pretorio is recognisable by the Torre del Porcellino, named after the sculpture at its summit. The side streets are home to workshops and shops selling alabaster, a material closely tied to Volterra.
Montalcino, fortresses, churches and Brunello
Montalcino is an icon of the Val d’Orcia, enclosed by powerful walls and celebrated for Brunello wine. The historic centre unfolds over different levels linked by stairways, with lanes constantly rising and falling before opening onto wide views of the vineyards.
Key sights include the Town Hall with its tall bell tower, the Church of Sant’Agostino, the neoclassical cathedral and the Sanctuary of Madonna del Soccorso, along with smaller churches dotted across the town.
A few kilometres away, the Abbey of Sant’Antimo is a Romanesque masterpiece set amid the countryside. Autumn is well suited to outings dedicated to truffles and porcini mushrooms in the surrounding woods, while tastings and winery visits give a clearer sense of the deep connection between the land and the wine’s designation.
Rapolano Terme, open-air relaxation in the Crete Senesi
Rapolano Terme brings together scenery and relaxation thanks to sulphurous springs that rise at around 39°C, supplying two thermal complexes with outdoor pools and treatment areas.
Later-season days add to the pleasure of a warm soak with views over the Crete Senesi, where autumn colours and steam create a memorable setting.
Other local sights include the Parish Church of San Vittore, the Church of San Bartolomeo and, in the fortified hamlet of Serre di Rapolano, the old gates, Palazzo Gori Martini, the Church of Saints Lorenzo and Andrea, and the imposing Grancia. A museum inside the Grancia tells the story of agriculture and olive oil in this part of Tuscany.
Article featured on The Wom Travel: In autunno questi borghi della Toscana sembrano usciti da un dipinto
