re: Italy Vacation November 2017 - May 2018 Timeframe

My wife and I (late 20's) did Rome-Naples-Florence-Verona-Venice for 17 days a couple of years ago.

If I could offer any advice on flights, if you can't find cheap-ish flights into Italy from your origin, just book a flight into another nearby European city and hop on one of the budget airlines to Italy.

We flew into Munich and spent a few days in Bavaria before catching a flight from Munich to Rome via Ryanair (cost about 40 Euro total). From there we booked trains from Rome to Naples and back north.

If you're not in your twenties and you've got an idea of the cities you want to visit, don't get the Eurail pass. Its not worth the extra money.

As far as cities to visit, if you're not going to devote time to seeing some of the more famous historic sites (the Colosseum, the Vatican, the forum, etc.) spend two nights there and move on.

I cannot stress this point enough, skip Naples. It has all the danger of New Orleans with half the charm. It is a city in decay with a swelling homeless population.
But, we did visit Pompeii. It is well worth the trip if you're in the area.
If I had the chance to do it again, I'd stay on the Amalfi (nearby) or on the islands (Ischia and Capri are beautiful).

As others have said, Florence is arguably my favorite spot on the trip. And Venice is worth a look if you're there. But the most interesting part was St. Mark's and the gondola ride. You can do that in a day.



One final note, if you're looking to be budget conscious on your trip, save on flights, save on hotel/hostel stays, but DO NOT skimp on food. You're going to be in arguably the most culinarily rich places on earth.
Eat, drink, ask for local specialties and house wines, experiment.