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Southern Italy itinerary for advice and critique

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So I have settled on an itinerary and am now looking for advice and critique. We're spending two weeks in Italy (this is our fifth trip and have been all over Tuscany, Venice and Rome previously). We're renting a villa in Cortona with friends for the first week and thought we would do southern Italy for the second week. Plan as follows:

7 nights - Cortona (day trips form here)

2 nights - Capri (plan is to drop rental car in Arrezzo and then take train to Naples and hydrofoil to Capri. Makes for a long travel day but then we figure Capri will be laid back since the island is small)

3 nights - Positano (day trip to Ravello and hire a guide/driver for our last day to take us to Pompei, Herculaneum and then drop us at Naples to catch a train to Rome)

2 nights - Rome (would only have a day here by the time we get in from Pompei, but really just stopping to eat a a couple favorite restaurants and shop a little before catching a flight home)

We like nice hotels (I'm not one of those "you're never in the room" types) and we're trying to figure out whether it's worth spending more in Capri or Positano? Capri we're considering La Scalinatella or La Minerva. Positano we're thinking Le Sirenuse or Il San Pietro.

Appreciate any thoughts on the hotels and the itinerary.

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