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Naples, Positano, Capri...and then some for 10 days?

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Hi Fodorites! We have used this site before and have had lots of success with our trips. We (meaning hubby and I) are planning a trip to Italy for our 50th birthday. We have seen Rome, Tuscany, Florence, Venice so now we would like to see the Almalfi Coast. My thoughts are as follows and our dates are flexible:

Plans are to go mid-late September although we are very flexible with dates.

Fly out of Naples - stay here for 3 nights
Onward to Positano - thinking private driver from Naples and staying here 4 nights
Take ferry to Capri - hopefully 3 nights here
Ferry back to Naples - fly home that day or stay overnight and fly back next day

1st question: We would like to visit Pompeii, Herculeum and maybe Ravello. Is it easiest to do from Naples or Positano? Should I take a night from Naples and add it to Positano or Capri instead?

2nd question: Places to stay? I know I could do a search on this site but are there any places that we absolutely should not miss? We would love romantic and quaint places to stay with terraces overlooking the sea. It's been 6 years since we have been wanting to go back so trying to make this vacation extra special without breaking the bank! :)

3rd question: Is a private driver worth doing to Positano. I'm assuming it's easiest to just fly into Naples rather than Rome. Is this correct?

4th question: Oh, and where else should we not miss? :)
Millie Grazie!

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