Arrival
Your tour begins in Pienza. The nearest major international airport to Pienza is Florence Airport (Aeroporto di Firenze-Peretola, FLR), about 145 km / 90 miles away, which is roughly a 2-hour drive.
Rome Fiumicino (Leonardo da Vinci International Airport, FCO) is about 220 km / 137 miles, 2.5–3 hours by car. It offers far more international connections than Florence.
You can take a high-speed or regional train from Rome or Florence to Chiusi–Chianciano Terme, which sits on the main Rome–Florence line. From Rome, it’s about 1 hour 45 minutes; from Florence, around 1 hour 20 minutes.
You can also take a regional train from Sienna to Buonconvento or Chiusi, but the Siena route generally involves slower trains and more connections.
From Chiusi–Chianciano Terme, take a regional bus (operated by Tiemme) towards Montepulciano and onward to Pienza. The total bus ride is roughly 1 hour, but departures are limited — often only a handful per day, especially on weekends or holidays.
If coming from Siena, you can catch a bus to Pienza via San Quirico d’Orcia, but this route is even less frequent.
Departure
Your tour ends in Castellina in Chianti, located 27kms or 17 miles from Sienna. You can take either a bus or train, or a direct taxi to reach Sienna.
You can also take a bus or train directly to Florence, located some 55kms ( 32mi) away.
The closest international airport is Florence Airport (FLR), about 65 km / 40 miles, 1.5 hours by car or bus. The airport is good for European and limited intercontinental flights.
The Rome International Airport is about 250 km / 155 miles, 3–3.5 hours by car or train. It is best for long-haul flights.
Siena has no high-speed train service, so the first leg is usually by bus or regional train:
To Florence – Direct bus (1h15–1h30) or regional train (1h30–1h45 with a change in Empoli). From Florence SMN station, connect to trains to Pisa, Rome, Milan, or Venice.
To Rome – Direct bus (3 hours) from Siena to Roma Tiburtina. Or train via Chiusi–Chianciano Terme (~3.5 hours total).