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Going for 2 weeks in June, need suggestions please

We have a group of 10 going to Italy in June. We know we want to break the trip up and stay in 2 villas, for roughly 1 week each, and take day trips. Two years ago we went to Scotland & Ireland, and drove to a new place each day..that was exhausting. We like the idea of having a home base. Just looking for input on locations you would recommend. One villa we looked at was in the Tuscany region, so I think we'll definitely do that. Should we fly into Rome and then take the train up to Tuscany? And any ideas for our 2nd location for a villa? Down to the boot, or up to Milan?? I just bought the Rick Steves Italy 2012 book lastnight, so am doing some reading, but this board has always been a great help too! Thanks in advance!
Katie

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