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Where in Tuscany to base ourselves for a week?

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Hi,

First of all - I know it sounds like I am, but I don't intend to ask a question many others have asked before. I have read so much about all the towns, mapped out distances, read countless posts on fodors etc. Still, I am confused where we should base ourselves. This is by and large because our profile is so dissimilar to most tourists who visit Tuscany. We are teetotalers, so there goes winery visits and Chianti craze; we are vegetarians, making our menu choices much more limited; and husband is a reluctant driver with even more reluctance to drive after dark.

So there it goes...

My husband and I are going to spend a week in Tuscany in end Oct/early Nov and wish to see the countryside and the several charming and famous towns. Focus is on relaxation, beautiful countryside, strolling in charming towns, visiting olive oil and cheese farms, eating good food (we are lacto-vegetarians with some tolerance for eggs as ingredients). Husband is not much into history, art and architecture.

Given a car affords more flexibility, we are going to hire one with automatic transmission from the Florence airport and move south. However, my husband is the only who would drive and he is extremely reluctant to drive too much (anything more than ~3-4 hours or so daily) and uncomfortable at the thought of driving after dark in countryside. Maybe it is the reputation of local drivers strengthened by the youtube videos and articles, or maybe it is because he is really not used to drive. Further, it is his first time in Italy. To him, our car having technical difficulty at 9 pm in the middle of countryside is high alert situation. To me, first of all I didn't even think of it happening. And if it does, it would be an adventure, and a story to tell for years to come! Anyway!

I was thinking it might be a good idea to split the week by staying right smack in the middle of a small town for 3 days and in the countryside for the rest. Potentially stay in San Gimignano for first 3 nights and do day trips to Volterra, Siena, Monteriggioni, etc and spend time in San Gimignano in the evenings when there are no more day-trippers left. Would give us option to walk around and have dinner without having to drive back late at night. For the latter part of the week, we could stay in a cottage / farm / villa in the countryside in Val d'orcia rather than within the walls of a town. But not too far from a nearby town, so that we can always drive over for dinner etc. It would be nice to stay where the owners live on site and dinners are offered. By the second half of the week, husband would feel more comfortable with the countryside driving so this should work out. We could visit Pienza, Montalcino, Montepulciano, etc.

Questions:

1. Is my line of thinking correct? Earlier, I wanted to rent a villa in a dreamy landscape in the countryside for a week and do day trips including nice dinners in different towns (and being part of passegiata) and going to nice farm restaurants specifically because of their acclaimed food. But maybe the modified approach could be more feasible practically given our constraints? How hard is it really to drive after dark, and locate addresses and drive down to restaurants in countryside specifically for dinner? Is it going to be unnerving rather than relaxing, this rent-a-car drive-in-tuscany week?

2. Any suggestions for specific towns / countryside for our home base as per approach above? I read that Pienza is a good idea because it is not too high up on a hill, and easily connected with main roads, making it easy to drive in and out? How about San Gimignano? Other towns?

3. Any pearls of wisdom on driving in tuscany? We have read up on road signs, driving rules, general Italy driving info online, etc.

Thanks for your patience if you made it till the end. And thanks in advance for understanding our predicament as newbie travelers and helping us.

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