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Where in Tuscany for ~6 day leisurely "home base" in May?

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I've scoured the forums for ideas and realize everyone's preferences, needs and itineraries are so individual!
Please offer your suggestions for a "home base" town in Tuscany from which we take day trips by car or train AND that meets some considerations I've outlined below.

Here are the considerations:
1) We have 6 full days between our arrival in Milan (morning of May 15) and when we depart on a cruise from Civitavecchia (May 21 about mid-day).
2) We've thought to explore Milan for the first day just to check it out --- and recover from jet-lag. Or, since we arrive pretty early on May 15, we could travel to our destination town right away. But, if we devote one day in Milan, we have only 5 days for Tuscany portion.
3) We've been to Florence before and enjoyed the wonderful museums. While I loved the city, we don't necessarily have to make a repeat visit this time.
4) We don't plan to visit Rome as we enjoyed several days there a few years ago.
5) Our objective in Tuscany --- or CT, Italian Riviera if you think it fits in-- is to experience the natural "Tuscan" beauty at a "leisurely" pace. Hence our desire to rent a car somewhere, possibly in Milan.
6) We've driven in Italy before, Venice to Verona and Padua and even in crazy Naples, so we're not intimidated (as long as we have GPS). I envision our driving would be highways to get from major point A to B, but then country roads to explore Tuscany with freedom.
7) Ideally we would make one town, but not more than two towns, as our "home base." From our home base we will make day trips around the countryside, and possibly to coastal towns, CT or other villages you recommend. Day trip could be by train if it makes more sense and is short.
8) Whatever base town we end up in should have enough going on that we can stroll and enjoy the Italian "vibe" should we choose not to make a day-excursion at all, and instead take a day "off" to enjoy a leisurely breakfast, gaze outside the hotel windows, read a book, have wine with lunch, take a nap.
9) And finally, on May 21 in the morning we have to make our way to Civitavecchia to arrive by around 12 pm to catch the cruise. Therefore our our home base would be convenient to either drive directly, or we'd return the car at a train station near our home base and take the train to Civitavecchia. Ideally we would avoid Rome if we took the train.

I know many of you have traveled extensively in the Tuscany, Umbria, Italian Riviera. I'm hoping you'll "see" in your mind's eye the perfect itinerary that fits the bill!

Thanks!!

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