Depends how many times you will be getting on and off the trains. For us it was less just to book our trains separately on the app. Just download their app and for instance if I knew what day we would be going from city to city for example a Monday. I just pick a Monday about a month out and got an estimate. I added all of them and it was just more practical for us to book online a day or two before. At least that’s my plan.
Planing a trip in Oct to Rome-Naples-Sicily-Florence is it worth it to purchase a Eurail Italy Pass, or better to book trains separately?
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A eurail pass makes sense if you are planning to do a lot of travelling within Italy. Your itinerary sounds like you may be better off purchasing point-to-point tickets as you are only travelling between 4 destinations. Railpasses also charge an additional seat reservation fee for any trips taken on high speed trains. Rome, Naples, Florence, and Sicily trips all primarily use high speed trains, so you would have to pay 10-20 euros extra for each trip if using a rail pass.
You can book these trips on Italiarail.com12 as point-to-point trips. Keep in mind the high speed train schedule is currently available up to September 17th. The later schedules will be released in the next 1-2 months, so please refrain from booking your trips until then.
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