Itinerary Review for First Trip

I think you have come up with a good itinerary but wonder about the four nights in Positano. It’s a pretty town but really doesn’t offer much for more than a 1 or 2 night stay. You say hire car from Naples to Positano, do you mean a car and driver or do you plan on getting a rental? The road is narrow, curvy and very busy and whoever is driving will be too busy concentrating to take advantage of the views. With a car/driver you at least get to enjoy the scenery. Also if a rental, parking in Positano is very limited unless you get lucky and find a hotel with parking.

I spent two nights in Positano mid-way through a tour and after having my hair done and doing some window shopping, I ended up spending a couple of hours on the beach and then when boredom set in went back to the hotel. Maybe stay in Amalfi, I think there is more to do and you can get a ferry to Capri from there. You can also get a train to Florence from Salerno which saves trekking back to Naples and takes about four hours. Or you could stay in Sorrento, again ferries run to Capri from there, but trying to get from there to Amalfi or Ravello is difficult unless you hire a car and driver.

Unless I misunderstood, you are flying into Rome, going way south of Rome, and then going back way north of Rome. You might consider trying to travel in a straight line to eliminate lost travel time backtracking. Perhaps fly into Venice, work your way south, and return from Naples. Just a thought.

Re: Flying into Rome and backtracking:
Yes this definitely not idea. I didn't want to end at Rome because I figure by that time we would both be pretty tired. Since I posted this and considered flight prices, we are now thinking of eliminating Venice from the trip and flying round trip out of Rome, so starting in Rome->Coast->Florence->Rome. What do you think?

Re: Four nights in Positano: By hire a car I meant a private driver. I've heard that it is not great to drive those roads yourself. Four nights in Positano felt like a lot to me as well but we want at least one day in the town to relax, one day to see Amalfi and Ravello, and one day to see Capri. I am concerned about getting stuck and missing out on experiences there if the weather is bad. Thank you for all of your input and let me know if you have any thoughts on the above. I'll look into the train from Salerno to Florence, that might work out the best for us regardless.

we are now thinking of eliminating Venice from the trip and flying round trip out of Rome

That being the case have you looked at your options to land in Rome and proceed onto Florence that day; then on to Salerno and the AC and finish in Rome.

It is easier to get to Florence than Positano, but if you arrive early enough and want Positano at the front end, you could take the reverse route ending in Rome.

Having stays in Rome at both ends of the trip adds an extra hotel move. If you do fly r/t Rome, you certainly need to be in Rome the night before.

We either go north or south of Rome in Italy, not both. I would drop the Amalfi Coast for more time in Tuscany; stay in a Tuscan town, not a day trip!
Aldo more time in Venice.

Our first trip was r/t to Rome, and we stayed there 5 days, then to Florence 6 days, then to Venice 4 days, with a high-speed train back to Rome at the break of dawn to make a noon flight. That last part was stressful; nobody was awake or operational that early in Venice, so we speed-hiked to the train station and sweated through our winter jackets. Train was fun, tho!

Now we bookend Rome to prevent rushing. 3 days at arrival, another 2 before we leave. There's always SO much to see/do/enjoy.

During Florence we did side trips/days to Pisa and Lucca. Siena would be easy, too, or Volterra. We haven't tried for the coast, but definitely heard having a driver is best. Buses look terrifying there!

It does seem like stretching to all four would make things a bit more hectic, but all sites should be interesting that time of year, so why not? Always assume you'll go back to fill in the stuff you didn't have time for on this trip. We got home from our latest Italy trip a month ago, and are still marking our Google Map with "Want to Go" spots that we missed or barely scratched the surface on.

I would agree with RT in/out of Rome being ok, as my last two trips have been the same. I have gone into Rome, IMMEDIATELY gone to Salerno for a relaxing time in a smaller city right off the bat, time in Salerno (and all those day trips), then WAY up north (either Venice or Lake Garda), then to Florence, then finishing out the trip in Rome before flying out again.

Wherever you end up wanting to go, put the time in your departure city at the end so you don't have to worry about getting to ANOTHER place the night before you leave and you don't have to change hotels an extra time. You're already "on the go" when you get to Italy, why not keep the "going" going and get to your first destination?