A good alternative to Siena and its countryside, but still using the car, is also the beautiful Chianti area, located between Florence and Siena. Chianti is a great base to explore Tuscany, but also the famous medieval hill town with towers, San Gimignano, is a very good base to visit Tuscany.

For travelers with a car, Siena or the surrounding Chianti region (towns like Greve or Panzano) are often considered the best bases in Tuscany. Siena is geographically central, making it an ideal "hub" for day trips to Florence (1 hour), the Val d'Orcia (1 hour), and San Gimignano (45 minutes). However, because Siena has strict "ZTL" (Limited Traffic Zones) in its historic center, many car travelers prefer staying just outside the walls or in a nearby "agriturismo" (farm stay). If you prefer a more rustic, countryside vibe, the area between Pienza and Montepulciano in the Val d'Orcia offers the most iconic Tuscan landscapes—think rolling hills and cypress-lined driveways—and easy parking. This southern base is perfect for exploring smaller medieval villages and vineyards. In 2026, splitting your stay between a northern base like San Gimignano and a southern base in the Val d'Orcia is a popular strategy to minimize driving time and maximize your immersion in the diverse Tuscan scenery.