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Cinque Terre to Montelcino

Only three months, 1 week to Italy!!! We've scheduled a car rental for pickup at 9:00 in LaSpezia and plan on spending the day driving Montalcino and sightseeing on the way. We would like to visit Volterra and/or SanGimignano. Stopping at both towns the same day might be a stretch, so which of those two hill towns do you like best? Or do you think it's possible to visit both the same day (sunset is not until 7:50pm)? We will be spending 2-3 nights in Montalcino. What would you recommend for destinations to explore outside of Montalcino? Pienza? Wineries? Other places? (We visited Sienna and Montepulciano last trip).

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Very smart doing a car from La Spezia to Montalcino. I love Volterra -- it's more "real" than San Gimignano IMHO. But San Gimignano is pretty. I think you have time to do both and be in Montalcino well before dinner. I think Rick Steves has a self-guided tour of Volterra. Follow that for a nice town tour. Montalcino activities:
- The abbey of Sant'Antimo (closes noon-3:00 so time your visit appropriately. You can hike there if you like, takes about 2 hours. Ask locally for directions. You can take a bus back so a one-way hike.) - Drive to Montepulciano thru Pienza. Bellissimo! - Thre are wineries. We didn't go to any because I won't drive if I am tasting. There is a great enoteca in town with 100 wines for tasting. Quite fun! (We only made it thru about 7.) - There's a nice little museum in Montalcino and the town i worth a tour; just walk around for a couple of hours. - Eat at Taverna Grappolo Blu. Fantastic!