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Hotels for Italy trip: help!

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We are planning to go to Italy this summer (fingers crossed). We are 2 adults, 3 teens.
We will get 2 rooms (the whole apartment thing doesn't appeal to us). Can someone recommend hotels? Budget is $300 total for two rooms? Which exact area in the following cities should we stay at? Is this a good itinerary for a good balance between art/history/nature? And how do we travel within the city?

Rome: 4 nights (fly in)
Amalfi coast (sorrentino?): 3 nights
Florence: 3 nights
Cinque terre: 2 nights
Venice: 2 nights (fly out)

Thanks!

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