We are in Siena for 4 days from 5 October and would love to do a hill town, wine or cinque terra tour from Siena. Any suggestions?
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San Francisco Bay Area (USA)
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Itineraries: follow towns in that order from Siena. North of Siena:
Itinerary 1 (famous hilltowns): Monteriggioni, Colle Val d'Elsa, San Gimignano, Volterra. Itinerary 2 (wine): Chianti Road (via Chiantigiana, State Highway SS 222) through Radda, Greve all the way to Florence. (you could actually do both in the same day, although it would be a brutal Mussolini tour. Actually no. 1 is challenging enough in a day) South of Siena: Itinerary 3 (hilltowns with wine): Montalcino (brunello wine), San Quirico, Pienza, Montepulciano, Chianciano Terme. You've got enough to be busy for 3 days. 5 Terre are not that close to Siena for a day trip. Doable but it would be a brutal Mussolini tour. By car you could make it to Riomaggiore in 2 1/2 hours one way, but only without being too gentle on the accelerator. By train forget it! You would need to change trains 3 times (at Empoli, Pisa and La Spezia).