First, allow me to apologize if this topic is already up for discussion. This is my first trip to Europe and I am a bit overwhelmed with all the planning. I will have 3 weeks in Italy starting in the Lake Maggiorre area (Bellagio/Milan) - but that will just be for a few nights - then it will be on to Venice for 3 days, Florence for 3 days, & Rome for 3 days; A possible 1 or 2 night stay in Cinque Terre; ending with a week long stay in a Positano villa on the Amalfi Coast. My dilemna at this point is transportation from point to point. Does the train system have adequate storage for your suitcase, etc? I've never ridden a train before so I didn't know if you had to "check" luggage like you do with airplanes or how all that worked. Would it be best to rent a car for the entire trip (although I have heard you should NOT drive in Florence or in Positano or in Cinque Terre) - so, if anyone has some great advice on the best forms of transportation between all these places, I'd really appreciate it.
I suggest you get a copy of Rick's "Europe Through the Back Door" and it will answer many of your questions in detail.
Ginger, haven't you ridden the Chattanooga choo-choo? (I'm showing my age). You are not alone in not riding a passenger train or hanging out in a train station. You will be stunned, shocked and amazed when you see this in action in Italy. You are about to embark on a whole new experience.
Don't fear the train stations or the train system. It's really easy and it works extremely well. All train carriages have overhead racks the whole length and on both sides for luggage storage so that's not a problem. Plenty of room. There is no security check of any kind. No checking of any kind is necessary. Just lug your luggage onto the carriage like you would a bus. These are not airplanes.
For Bellagio, you'll have to take a local train from Milan Centrale to Varenna and then a ferry to Bellagio. You'll need to do this in reverse to come out to Milan. The rest of your trip looks great. Lot's of nice high-speed Eurostar trains.
For tickets, you can get them when you get there. Many North Americans sit back and say "not us". We want our tickets in hand before we go. Still, once you learn to play in the train stations, it's soooo easy. Plus, if you buy in advance, you can sometimes get the AMICA fare which is a 20% discount. I suggest that you use the self-service machine in the large stations. It will prompt you in English, make your seat reservations and accept your American credit card. If you must have your tickets in advance, you can buy most of them on www.italiarail.com. You won't be able to buy the tickets for the private Circumvesuviana train from Naples to Sorrento in advance. From Sorrento to Positano, you can take either the SITA bus or the ferry. No train. You'll love the whole experience.