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Looking for advice about 2 week solo trip to Italy

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This will be my first major solo trip. I'm a 30 year old male from the US, planning to go in late May and early June when it will be warm, but not quite the peak busy season yet. I've been to London, Tokyo, NYC, and few other places kind of solo, but have usually either had people I knew to meet up with there for part of the trips or they've just been very short trips. I've heard the pickpocketing can be really bad in Italy which will be a big change of pace from Tokyo, but I did get a little practice preparing for pickpockets during my short London trip. Hopefully wearing my backpack in front of me in crowded areas, a money belt and belt loop zip pockets will be good enough.

My big inspirations for going to Italy are food, history, and the scenery. I'm looking forward to trying some of the best pizza and pasta I've ever had, and visiting a lot of the ancient sites there such as the Colloseum, Pompeii, Paestum, etc. I'm not real big on art museums or particularly religious, but I do plan to visit Vatican City, some of the nice cathedrals, and major works of art. I'd also like to be able to see a lot of the beautiful countryside and coastal towns. I can't see the crowds bothering me too much since I loved Tokyo and NYC; part of what I loved about them was all the unique stores and shopping centers around, and something exciting to see on practically every block. It was great in Tokyo to get submersed in a whole nother culture, and all the little quirky things like maid cafes or the futuristic toilets. While I don't expect the food, history or scenery of Italy to let me down, I'd be open to suggestions of other really cool or unique things to do there.

My basic itinerary at this point includes possibly flying into Venice and spending a couple days there, then spending about 3 days in Florence, 4 days in Rome, and 3 days in Naples. It could be nice to visit St Mark's Basilica in Venice, but I'd be going to visit Venice more than anything just to say I was there, have heard that the food is expensive and mediocre, and get the impression it's a better city for couples to visit. I was planning to fly out of Rome since I've heard the Naples airport is bad, but am open to suggestions about which airports would be most convenient to fly in or out of. I don't plan to bring any major luggage with me; pretty much just a carry-on backpack and a slightly larger backpack on wheels. But the inconvenience of even having to carry a small amount of luggage on trains at risk of theft, and between multiple different hotels, worries me a bit.

Hoping to make day trips to Pompeii and Paestum, Cinque Terre or Amalfi Coast, maybe some of the countryside towns of Tuscany. Paestum might be a bit difficult to work in, since from what I gather there aren't too many quick bus routes there and hiring a private driver can easily exceed 300 Euros. I don't look forward to all the garbage and extra crime Naples purportedly has, but am drawn there for all the incredible pizza, the archaeological museum, and great local day trips nearby. I don't have a lot in particular planned so far outside of what I've already mentioned, except the Duomo and Uffizi in Florence, and the underground tour of the colloseum. I've generally preferred independently exploring places in previous trips I've made, but would be glad to hear about any highly recommended tours of the big attractions.

Any suggestions appreciated!

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