mactire
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I've been to Naples twice this year, each time for a week, and never visited Sorrento (or even left the city). Naples is a great city, but if you're looking for a truly relaxing experience, Sorrento and such might be the better choice.
You can spend weeks in Naples seeing sights and having a good time. I'd recommend staying close to the university, around Piazzetta Nilo. No idea if there are upper class hotels, but there very likely are. Anyway, it's super central--but nonetheless you should expect to walk a fair bit in Naples; public transport usually doesn't make much sense and you're better off walking--, quite touristy of course, lively student life, great cafés, a lot of sights in close proximity. The better pizzerias are very close too, if you're into that. Streets are full and vibrant at night. If you need help with sights to see, I can help you. Regarding evening activities, I think you're looking for more "upper class" options. If you're looking for a down to earth activity with a beautiful sunset, let me know.
I'll be there in May, would love suggestions if you have any. A great café, good pastries, a market/brocante, bookshop or record shop if you'd care to share? As for down to earth, that'd be great too. The last time I was there I went to cafés and restaurants at random, or down streets from the Corso Umberto I.