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Tuscany Itinerary - what do you think?

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I've been reading through so many guidebooks, I think my eyes are rolling back in my head! I have an idea of what I want to do through Tuscany, but would love a little advice on a few things. For the Tuscany portion of my trip, I am looking for relaxation, experiencing Tuscan life, beautiful sights and maybe a little bit of shopping for local goods (early Christmas shopping for folks at home), good food, soaking it all in and generally refreshing and filling my soul. Possibly some art/history, but will be getting my fill of that in Florence and Rome, so not as important to me through Tuscany. Most of eating out will be lunch/snacks through here, as I'll probably avail myself of my kitchen at Fonte Bertusi for dinner at home (I enjoy cooking with fresh, local ingredients). I'm imagining alot of casual roaming around villages and sitting in piazzas drinking espresso or eating gelato, while watching life pass by and swirl around.

This is what I'm thinking:

Monday am: Leave B&B in Florence - pick up rental car. I will be staying in an agriturisimo (Fonte Bertusi) outside of Pienza, but have two thoughts of how to get there. The more out of the way route - Volterra for a half a day and then on to Pienza. Or - the more direct route - drive through Chianti (mostly for the views, will be driving on my own, so wine tasting will not really be on the agenda) to Siena for a bit and then on to Pienza. I'm kind of leaning towards Volterra, but how realistic is that really?

Tuesday: Cortona for the better part of the day and then perhaps explore Pienza a bit before heading back to Fonte Bertusi. Maybe poke around Fonte Bertusi (depending on when I get back).

Wednesday: Definitely want to visit Sant' Antimo Abbey (hoping to hear the Gregorian chants) but then not sure of whether to visit Buonconvento or San Quirico - both sound lovely. Any opinions on either? Or should I pop up to Siena (if I don't visit on my way down from Florence)?

Thursday: Montepulciano (I believe it is market day!) and Chianciano Terme (a friend just visited and really enjoyed the spa treatments - I'm intrigued).

Friday: Check out of Fonte Bertusi - on to Orvieto - drop off the car, visit the town and check out the ceramics - catch a train to Rome.

Is this reasonable without running my little legs off or am I overreaching? Is there something that I've completely missed (as in "how could you go to Tuscany and not....?")

Thanks so much for any advice... I'm getting really excited for the trip!

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