Sarteano
Sarteano is a small medieval gem nestled between the Val di Chiana and Val d'Orcia: stone alleyways, panoramic views and an authentic atmosphere far from the crowds.
Not to be missed: the Castle with its sweeping views over the hills, the small but rich archaeological museum and the nearby Etruscan Necropolis of Pianacce, a testament to an ancient history.
Guide to Sarteano →
Montepulciano
Famous for its Vino Nobile, Montepulciano is an elegant hilltop town rich in Renaissance palaces and historic cellars carved into the rock. The long main street leads up to Piazza Grande, one of the most scenic squares in Tuscany.
- Vino Nobile di Montepulciano DOCG
- Piazza Grande and Cathedral
- Historic underground cellars
- Summer festivals and local events
San Casciano dei Bagni
Known since Roman times for its natural thermal springs, San Casciano dei Bagni combines wellness, nature and history. The open-air pools at 40°C are unforgettable, especially at sunset.
Recent archaeological excavations have unearthed extraordinary Etruscan and Roman finds at the Bagno Grande sanctuary — one of the most significant discoveries of recent decades.
Guide to San Casciano →
Pienza
The "ideal Renaissance city" commissioned by Pope Pius II is an architectural gem overlooking the Val d'Orcia. Its streets are fragrant with Pecorino cheese and open onto breathtaking views of Tuscany's most photographed hills.
- UNESCO World Heritage Site
- Pecorino di Pienza DOP
- Piazza Pio II and Cathedral
- Spectacular Val d'Orcia views
Montalcino & Brunello
World-renowned for its Brunello wine, Montalcino commands the Val d'Orcia from the heights of its medieval fortress. The surrounding hillside vineyards and historic cellars make it an essential stop for wine lovers.
3 days in Val d'Orcia →
Città della Pieve
An elegant Umbrian village, birthplace of Perugino — master of Raphael. Narrow brick-red streets, the Adoration of the Magi fresco and what is said to be Italy's narrowest alleyway. Perfect for a romantic stroll between art and silence.
Cortona
Made famous by "Under the Tuscan Sun", Cortona is one of the most panoramic villages in the region. Steep streets, medieval palaces, museums and a sweeping view over the Val di Chiana. The sunset from its terraces is among the most moving experiences in the area.
The most beautiful villages →
Orvieto
With its magnificent Gothic Cathedral — one of the finest in Italy — Orvieto crowns a tufa rock cliff above the valley. St Patrick's Well — 60 metres deep with a double helix staircase — is a masterpiece of Renaissance engineering.
Siena
With its Piazza del Campo, Siena is one of the best-preserved medieval cities in Europe. The Cathedral and the Palio (held every summer) make it an unmissable stop for anyone visiting Tuscany.
Assisi
Birthplace of St Francis and St Clare, Assisi is one of the most important spiritual destinations in Europe. The Basilica with its frescoes by Giotto and Cimabue is an absolute masterpiece. Walking its streets feels like stepping into a suspended moment in time.