From the Leaning Tower via Lucca and San Gimignano to Siena and Montepulciano — Tuscany by rental car from Pisa airport.
Tuscany was made for road trips: rolling hills, cypress lanes, medieval towns and endless vineyards. The ideal starting point is Pisa: pick up your rental car right at the airport (via YuppiRent, no credit card and no deposit needed).
The route: Pisa → Lucca (cycle the intact city walls) → Florence (park at Villa Costanza, avoid the ZTL zones) → San Gimignano and Volterra → Siena (Piazza del Campo) → Val d'Orcia with Montepulciano and Pienza → back via Bolgheri and the Etruscan coast.
Practical tips: compact cars from €16/day with unlimited mileage and full coverage, watch out for ZTL zones in historic centres, and book 2 weeks ahead in high season. Buon viaggio!

