Pontassieve sits at the confluence of the Arno and the Sieve, fourteen kilometres east of Florence. The name says everything: it is the bridge — the Medici Bridge — over the Sieve, built in 1555 by order of Cosimo I and still in use. The town that grew up around it is the entry point to the Sieve valley and the heart of the small but prestigious Chianti Rufina wine zone.
The walled medieval core has held its shape. The 14th-century Florentine fortification, the Castello di San Michele Arcangelo al Ponte a Sieve, still shows three gates — Porta dell'Orologio to the east, Porta di Filicaia to the south, Porta Fiorentina to the west — and the Palazzo Sansoni-Trombetta, now the town hall, at its centre. A walk through any of the gates leads quickly out into the open country of the Sieve valley.
The wider commune climbs into wooded ridges on either side of the river. Old villas and isolated parish churches — Villa della Pievecchia, Pieve di San Lorenzo at Montefiesole, the abandoned tower of Montebonello, the Pieve at Acone — punctuate the hills, linked by the network of CAI footpaths described in the Footpaths section. The whole Chianti Rufina wine zone fans out east from the town, with the Frescobaldi castle at Nipozzano and Castello del Trebbio open to visitors by appointment.
Use Pontassieve as a base for the valley, not as a destination in itself. The town is workmanlike and prosperous, with a busy weekly market on Wednesdays and a handful of decent osterias around the centre, but its real value is as a station stop on the Florence line with a quieter side of Tuscany at its back door.