Help w/ 3 Week Italy Itinerary Order & Train Vs Car
 

Really need help deciding on how to order the following locations for a 3 week Italy trip in September. Will determine where we fly into/out of after itinerary is determined and do not need to arrive/depart from same location. Plan to fly on a Friday, arriving Saturday, and depart on a Sunday, so that gives us 22 nights total. Would like to do 5 nights Dolomites, 3-4 nights Lake Como, 3-4 nights Cinque Terre, 5 nights Positano (or other Amalfi Coast town). So that gives us 5 additional nights to add on another city and/or additional nights LC or CT. Need help deciding best way to order this itinerary to maximize time in each location. Also, which legs of this trip would you rent a car vs take a train. We will need a car for the Dolomites, and love a good road trip and aren't afraid to drive the entire trip, just not sure about convenience of having a car in CT or AC. Thought about flying into Pisa or Genoa, then ordering CT -> LC ->DOL -> Rome or Florence -> AC -> Home from Naples or Rome. That's just quite a trip from DOL TO Rome or AC. Or, fly into Naples, then do AC, then travel up the coast to CT -> LC -> DOL -> Home from Venice or Milan. We've been to Italy once and visited Rome, Venice, Milan, all by train, then took the train from Milan up to Switzerland. CT, AC, DOL, LC are non-negotiables for this trip. Please help!

Plenty of options, look at flying into Milan, go to lakes, then pick up car for Dolomites. Drop car at La Spezia for Cinque Terre, then Rome, then AC if flying out of Naples, reverse AC and Rome if not.
How early/late in September might be a factor--hope fully some of the Dolomites experts will weigh in.

Thinking first or second weekend in September, and yeah that's exactly why I thought we should do Dolomites early in the trip, for hopefully somewhat better weather for hiking and such. Thanks for the suggestions!

You've pick places that are quite far apart and somewhat remote, and you'll spend many hours on trains. (You don't really want or certainly need a car anywhere but the Dolomites.) I would prefer less criss-crossing. The Dolomites are about halfway between Milan and Munich. I would fly into Munich and train to Bolzano (4.5 hours, it would be a few minutes longer from Malpensa). If you're going to have to connect somewhere in Europe anyway, fly into Verona. Do a round-trip car rental from Bolzano or Verona (round-trip to avoid a one-way rental surcharge plus some fuel charges and tolls). Then train to Varenna (or Como, depending on where you'd stay), train to the CT, train to the AC (an all-day trek). Fly to home from Naples or Rome.

Picking up a rental car at Lake Como is only convenient if you're staying in or near the town of Como.

If you flew into Verona, you might consider exploring Lake Garda rather than Lake Como.

You can get estimated fuel costs and tolls at viamichelin.com.

I wouldn't add any destinations to your list. I would add at least one additional night to the Dolomites, and allow one night to position yourselves close to the departure airport, esp. if Rome.

We did something like this a few years ago: Flew into Venice and drove a car from there to Bolzano - then Lake Como - then dropped the car in Genoa. You could do the same but drop the car in La Spezia, you won't want it in the CT. You could also add Milan but the car is no help there either.

South of the CT you could add Florence, or not. Either way you could take the train to Positano and fly out from Naples or Rome.