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Need area and hotel recommendations, please!

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Now that I have my itinerary (have 1 more night to figure out but will figure that out later), I need to ask you all for help again! Which area should we stay in while visiting the below cities? Which hotels? My husband is very picky and a hotel lover. I'm less picky and will consider apartments. Unless we really have to, we want to stick to hotels. We also must have AC (we're traveling in the summer) and we have 3 teens (14, 14, 15). Would like to keep our per night budget for a room $300 or less. Also, would like to be close to the sites (but don't have to be in the middle of it all, we enjoy walking!). If you have a great apartment recommendation, please do share. My guess is that as the dollar signs start to become real, hubby will start to consider an apartment :-)

1 night Milan and next day we travel to Venice,
3 nights Venice (day trip to Verona), train to Florence
4 nights Florence (day trip to Sienna, Pisa- yes, my kids want to do that corny picture, Cinque Terre),- depending on lodging options we'll either take the train straight to Sorrento or Rome
4 nights Sorrento,
5 nights Rome (fly out of Rome)

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