From Pontassieve, continue through the Reggellese area not far from the Vallombrosa Forest, where there are the parish churches of San Pietro a Pitiana and San Pietro a Cascia, which are home to the splendid Triptych of San Giovenale, an early work by Masaccio.
Following the Via Cassia, we arrive at the provincial road 1 Setteponti, which leads to Pian di Scò, with the Romanesque parish church of S. Maria in the Old Town, first mentioned in a document from 1008. Blind arches and two single-light windows adorn the facade. The interior, with its three naves, is marked by columns with figured capitals. On the left wall is a fresco depicting a Madonna Enthroned with Child dating from around 1400, by Paolo Schiavo.
Continuing towards Castelfranco di Sopra, the Abbey of San Salvatore a Soffena, a religious building built in the 14th century on a pre-existing castle deserves a visit and testifies to the presence of a Vallombrosan community in the Upper Valdarno. Inside there are priceless frescoes by Liberato da Rieti, Bicci di Lorenzo and Giovanni di Ser Giovanni known as Lo Scheggia (15th century). The latter was Masaccio’s younger brother. Next to the Abbey is the monastery, where recent archaeological digs have brought to light medieval and Renaissance tombs.
Once arrived in Castelfranco, you can admire the peculiar town planning, traditionally attributed to Arnolfo di Cambio, with a regular chessboard layout. It was once surrounded by walls, towers and gates, but only two remain today. Don’t miss the Oratory dedicated to San Filippo Neri (18th century), who was born here in 1515.