Pontassieve preserves the three gateways of its 14th-century Florentine fortified wall — Porta dell'Orologio (east), Porta di Filicaia (south), and Porta Fiorentina (west) — and a Medici bridge over the Sieve from the 16th century. The town is a base for walking routes into the surrounding hills, marked by the Italian Alpine Club (CAI) and local excursion groups. The Chianti Rufina wine zone begins here; several wineries in the valley are open for tastings.