Naples

We were there last summer. Found it kind of dirty and gritty but not particularly unsafe. We used the tram and buses without any problems. We are 65 and have done about 300 days over past 15 or so years and have never had any problems anywhere. Maybe we look like we have anything to be bother for. Maybe just lucky.

I have heard the stories about Naples and was hesitant to stay there. I decided to stay in Sorrento instead. I will pass through Naples from Rome to do the museums during the day and then head to Sorrento (1 hour away) to stay the night. Sorrento sounds like a great place to use as a starting off point for Mount Vesuvuis and Pompei, which are the main reasons I am headed south.

As for crime - Naples is not unsafe! You do need to watch for pickpockets more than in other parts of Italy - but I felt more likely to be pickpocketed in Paris than in Naples. The thing to remember is that while having your pocket picked is completed unpleasant, you won't even know it happened and you will be safe from physical harm. (As a random aside, of all the people I know who've travelled to all sorts of far-flung and "dangerous" places the only person I've ever known to be pickpocketed was my mom, in one of the nicest parts of the Upper East Side of Manhattan!)

As for the dirt, it depends on the type of people and travellers you are. Cities don't bother me - I live in New York and before that Washington, DC (and not in the nicest parts!). I love cities and think the dirt and the grime are part of the charm and authenticity. I'll take dirty, interesting Naples over boring Sorrento any day. If nothing else, the pizza, museums, architecture etc are worth day trips.