Pontassieve spreads over the banks of the Sieve River where it meets the Arno, east of Florence. It was historically a crossroads town, first during the Florentine Republic and then in the post-war period when the railroad line was built. It's the principle town in the valley and still boasts a twice-weekly market (Wednesdays and Saturdays). Pontassieve means "bridge on the Sieve River" and it's most noted landmark is the stone arched bridge that connects the two banks of the river together.

The town retains its antique characteristics like gateways, palaces and a castle dating back to 1399. While it has developed industry, most notably glassworks, it is still an agricultural area filled with olive trees and grape vines. This is the Chianti zone and there are several well-known wineries in the area dedicated to producing Tuscany's famous vintages.

Just outside is the fairy book castle, Castello di Torre a Decima, with a little stone chapel in the midst of vineyards and surrounded by stately cypress trees. The encircling hills are classic Tuscan landscapes. The church of the Madonna del Sasso was built in 1484 in Florentine style and has been attributed with miraculous apparitions.

Pontassieve offers a wine market every June and an annual summer music festival. It's convenient location connects it to Florence, Arezzo, and the Chianti hills.

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