Useful Travel Books
Get something like the Lonely Planet or Rough Guide title for the country or region to figure out what major areas to see, and how to get around and where to stay. They will at least lead you to the highlights of what to see.
For really getting into the details, and there are a lot of details in Italian history and art, I have found the Blue Guides to be extremely useful for sight-by-sight guides to art museums and the local architecture. Buy used ones cheaply, you're looking at old buildings and artworks.
I had picked up a conveniently small and portable Random House pocket Italian Dictionary just before leaving. I bought it quickly, and only looked through it in detail once I was in Italy. This small dictionary was convenient, but not very useful! It could tell me the Italian words for Jehovah's Witness, wiretap, wire recorder, cuspidor or spitton (that one is sputacchièra), but it did not contain many of the words I tried to look up.
It patiently explained that the Italian word for opossum is opòssum, despite that animal's range being limited to North America. How is this useful?
- "Mi scusi, is that dead animal beside the road an opòssum?"
- "No, signore, it is a tasso (badger)".
It also tells you that decalcomania is the Italian word for decalcomania. That sounds like an obsession with calcium removal, but it refers to an art technique by which engravings and prints may be transferred to pottery or other material, a technique developed in England about 1750 and exported to the United States about 1865. That's not really the sort of thing you need when finding your way around Italy for the first time.
In the back it lists some rather quaint "useful phrases" including "I want to send a telegram" and how to ask if travelers' checks are accepted, but it has nothing about credit cards. It also explains that one chilolitro is equal to 264.18 gallons. That might be useful to mariners, although it doesn't say whether that's British or U.S. gallons.
I was very glad that I had also brought my far more helpful Bantam New College Italian/English Dictionary, sometimes titled as Mondadori's. It's still no larger than a small paperback novel, and it contains the words that you need.