Torn between two lovers

I've done both ways of blitzing around towns and moving every 2 days, and relaxing in a town for 4-5 days. I enjoy either. If you want to see a lot of stuff and don't mind moving, then go for it and visit all the towns.

For flying don't look at round trip in and out of Milan or in and out of Rome. You'll waste time traveling the last day back to Milan. Fly open jaw and see the costs. You should Def fly into Milan but look at flying home from Rome or Naples. I went into Milan and out of Rome last week. The cost was not as expesnvie as in/out of Rome but not as cheap as in/out of Milan. It was in the middle and not having to travel long distance at the end of trip is worth it.

Those places are quite far apart. Also, it may not be an ideal time of year to see the Dolomites. And while a car might be helpful in the Dolomites and Tuscany, it will be a pain elsewhere.

If you do end up staying in Amalfi and flying out of Milan you might think about taking a cheap flight from Naples to Milan to save time.

Be sure to check which hotels are open in the Dolomites in October. We were there once in October and almost everything was closed as this is the only time that the hotel owners can take a vacation. There was also no heat in the hotels where we stayed as it was too early in the year for it to be turned on and that was very unpleasant. I would suggest the Dolomites for another time and another trip.

Try flying into Naples, see the Amalfi Coast area first, then head north and end up flying out of Milano.