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Need help determining best locations for two one-week villa rentals in Ita

We are planning a two-week trip to Italy in June for 4 adults and 3 young kids (6,4,2). My father has never left the US but has always wanted to visit Italy, so this is his once-in-a-lifetime trip. We want to find two locations where we can rent a villa and experience life in a small town but are well-situated for day trips to major points of interest. We plan to spend one week in Tuscany but are not sure the best small town to be near (we'll want day trips to Florence, Siena and/or Lucca, and perhaps the coast). Week two is trickier; we would like to see Venice and perhaps take a day trip into Austria but also enjoy some of the natural beauty of the Dolomites. We are badly in need of some recommendations of where to make our home base for this week, or if there is a better choice for Week 2, we would love suggestions! I should mention that our 2 year old is exceptionally active and will probably not do well in crowded settings like museums and that my FIL has some interest in a day trip to another country such as Austria.

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One thought, while many people like day tripping most towns are a zoo in the daytime and then become magic at night after the daytrippers leave.By staying in a number of places you can see the towns in the evening.