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CT / Tuscany Itinerary Question

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My husband & I will be in Italy this May (my first time, husband's second time) and will just be visiting Venice and Rome, with a day stop to Florence, during our 10 night stay. I now prefer "slow" travel as opposed to lots of moving around as we did that for many years! We pretty much have everything planned out with so much help from these forums. With 4 nights in Venice and 6 nights in Rome, I think we will have enough time to do and see the things that are of most interest to us.

My question actually is pertaining to the logistics of my trip to Italy which I am planning for next May (we vacation about the same time each year). I so much enjoy planning and researching our trips ... to me that's half the fun! This year's trip is 2 years in the making!

In any event, next year I am thinking Cinque Terre and Tuscany. I will have 10, 11 nights tops for this trip. I was thinking maybe 4 nights CT / 6 nights Tuscany:

I was hoping to visit Volt/San Gimig; Chianti area (not sure which town/s); Pienza area; maybe Arrezzo so I was thinking maybe:

nights 1-4: CT (not sure where yet) - no car
nights 5-6: San Gim (visit Volterra first then head to SG) - rent car in CT
nights 7-10: Siena area with a few day trips
night 11: Florence

My question for you would be would I be better off having just 1 base and visiting other towns as day trips? I am not set on the Siena area for a base if there is a location that would make better sense. What would be the best way to visit the areas on my list in 11 nights? What places could be easily grouped in a day trip?

Thank you!!

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