Getting in

• Florence Airport: Rent a car here if Pienza is more than a one-night stop: it is about 1 hour 45 minutes–2 hours by road. Without a car, tram to Firenze Santa Maria Novella, train to Chiusi–Chianciano Terme, then pre-book the 45–50 minute road transfer; viable, but clumsy for exploring Val d’Orcia.
• Rome Fiumicino Airport: Best only if Rome is already on the trip. Drive 2¼–3 hours, or take the airport train into Rome and continue by rail to Chiusi–Chianciano Terme; expect 3½–4½ hours to Chiusi before the final transfer. Skip private airport transfers unless a group is splitting the bill.
• Pisa Airport: Usually the wrong airport for Pienza. Driving takes roughly 2½–3 hours and rail adds an awkward Florence-area interchange. Use it only if the airfare saving is genuinely large or Pisa/Lucca is already on the itinerary.
• Chiusi–Chianciano Terme station: This is the railhead to aim for on the Florence–Rome line. Pre-arrange a taxi/NCC or rent a car for Pienza: 45–50 minutes, roughly €70–90 per vehicle. The cheaper bus routing via Montepulciano is fragile, especially on Sundays.
• Siena: For a car-free Siena day trip, take Autolinee Toscane line 112 via San Quirico: about 1 hour 10 minutes from Porta Pispini to Pienza. Check the live timetable in the AT Bus app; this is rural service, not a frequent shuttle.