Is a rail pass worth it in Italy?

Usually not. Italian point-to-point fares are cheap, especially bought in advance, and Eurail passes still require you to pay a seat reservation on every high-speed train — so the pass costs more and then charges you again. A pass can make sense if you're taking many long journeys across several countries, or if you genuinely can't plan and want to decide each morning. For the standard Italy trip of four or five intercity hops, buy individual tickets. Do the arithmetic on your actual route before buying; it takes ten minutes and usually saves a couple of hundred dollars.