Best Way to Travel from Cinque Terre, Rome, Amalfi Coast and Sicily

Sicily needs at least 8 to 10 days at the very minimum. It's also far from the rest (flying is the best option), therefore unless you can increase the length of your vacation you should drop it altogether.
The airports closest to Cinque Terre are Pisa and Genoa, not Florence.
Unlike the US, the way you travel through Italy is generally by train, and some more secluded towns, by bus.
From the Cinque Terre to Rome you would use a train. To the Amalfi coast you would also use trains to Sorrento or Salerno, then a bus to the Amalfi coast (which has no rail). You need at least 3 or 4 nights to see Rome. It's like Chicago. Big.

Thanks Roberto. I may have to suggest taking Sicily off the schedule for now, that allows us to add a day or two onto Rome. Myself and another traveler went to Italy last June and did Rome, Cinque Terre, Florence, etc. and have a good grasp on how to travel around. Maybe we can fly into Pisa or Genoa and go from there.

As Roberto suggested, you should consider flying into Pisa or Genoa and start in the CT. From there, take the train to Rome and then another train to the Amalfi Coast. If you finish your trip there, check for return flights from Naples back to the US.

jenna,

A few comments to add.

The "cities of the Cinque Terre" are better described as five small towns. Monterosso is a good choice (how can you tell it's my favourite of the five).

Skipping Sicily is most definitely a good plan! It will take you the better part of a day to get there, allowing only one full day for sightseeing and then you'd have to move on to your next stop. That's not worth the effort or the cost. I'd suggest saving Sicily for another trip when you can devote more time to it. Add one day from Sicily to the Cinque Terre and one day to Rome.

Given the places you want to visit, flying inbound to Pisa and outbound from Rome or Naples would be the best idea. I don't know whether direct flights to Pisa are available from your area, but I'm sure one of the others will be able to provide that information.

As Roberto mentioned, using trains is the best method of travel in the majority of cases. They're frequent and fast (especially the high speed versions which travel at up to 300 km/h). You can check the routes you'll be travelling on the Bahn.de or Trenitalia websites.

In order to plan the most efficient touring, I'd highly recommend packing along a copy of the RS Italy guidebook. There's an enormous amount of good information there!

If you haven't travelled by train or other public transit in Italy before, there are some potentially expensive "caveats" to be aware of. You'll need to be aware of those.

Check the various connections for Pisa and Genoa. You won't go there straight from the US and would change planes someplace in Europe before connecting there. Also check the times you arrive at those airports and get to the CT. Last time there 7 of us flew into Milan straight from the US and arrived in the morning and we trained down to the CT. We got in by lunch. Our flight and cost was cheaper then our 8th person who went from Miami to Lisbon to Pisa, then trained to the CT. She didn't meet us until after 7pm. Her flight from Lisbon to Pisa was in the late afternoon. Then she still had an hour train ride to us. So check the schedules as even though Milan is further it could be cheaper and arrive earlier.

Thank you all for the advice! After looking over these, we have decided to skip Sicily for now and come back to that in a few years. Right now, our trip looks like: Fly into Milan or Florence from Chicago (since flying into a smaller airport is more expensive), go down to Cinque Terre for a few nights. Then make our way to Rome for 3 nights, then set our way down to Naples for a night (Pompeii half-day tour), and finish with Amalfi Coast for 3-4 nights. Potentially fly out of Naples?

Our flight situation is TBD, but our trip looks more travel-friendly now that we aren't having to spend a day traveling to Sicily. Guess we will have to come back again :)

Monterosso is okay, but not the loveliest of the Cinque Terre, because it can easily be reached by car. The same is true of Riomaggiore on the south. My favorites were Vernazza and Manarola. If you possibly can, walk the entire distance, town to town, and spend the night in at least those two gems. If you do it from south to north, then make the return trip by ferry -- it's a hoot. You can also use the train if you want to skip a town.

Many people devote a single day to the Cinque Terre. That's absurd. It's worth a week's vacation time.

Pisa has a direct flight from New York JFK with Delta from June through August. Not sure if it would work for you.
From Chicago, you might consider United/Lufthansa. Lufthansa flies to both GOA (from Frankfurt) and PSA (from Munich).
Everything flies to Rome of course.
As you could see, different people have different tastes when it comes to the Cinque Terre. However all of them can be reached by car, so that is not a discriminating factor. The only thing that changes is the availability of parking, which is limited everywhere, but less so in Monterosso or Riomaggiore.