Pisa – Lucca – Montecatini Terme – Florence – Arezzo – Siena – Castellina in Chianti – San Gimignano
This classic route circles Tuscany's green, sweeping Chianti region. Follow cypress-clad roads through undulating vineyards and hill towns with a stop in the Renaissance mothership of Florence. From Pisa, head northeast to the medieval town of Lucca (birthplace of Puccini) and Montecatini Terme to take a dip in the thermal baths. Set aside a few days to explore Florence before looping around to Arezzo and its impressive antique market, and the medieval city of Siena with its stunning 12th-century Piazza del Duomo. The small town of Castellina in Chianti is a perfect stop between Siena and San Gimignano, which is known as the Manhattan of Italy for its 14 soaring towers. From here, it's a short and scenic drive back to Pisa.