Italy Trip in May - 23 days - edited

Hi Scott -
Good lookin' trip you have here, and lots of good questions! Without getting into hotels, classes and restaurants (a browse through the forums is a good place to start: use the search box at the tiptop of the page), I would cut the Amalfi: it's an outlier, and the coast really requires more than the 1 full day you've given it.

I also highly recommend staying in Milan on your last night. You don't want to be far away from the airport the day of an international flight in case of a transport strike or other unexpected snag. If it were me? I'd take those two nights from Amalfi, add one to Rome (oodles to see there) and the other to Milan (Day 22).

A few hotel and apartment suggestions:

Varenna--- we have twice stayed in the "mansard" top floor room in Casa Rossa at Albergo Milano:

https://www.varenna.net/ITA/Casarossa-mansarda.html

It is large, bright and airy, with a huge balcony, useable kitchen corner, and trendy modern bathroom. Lots of steps to reach it but the views over the lake are great. This is a separate building from the hotel but you go over there for breakfast.

For CT, you said Vernazza but we much preferred Manarola, and loved our balcony room at La Torretta. It was among the lowest -priced rooms but had a great sea view ( they describe it as partial) and we particularly enjoyed breakfast on our balcony. I think it was Room 6 but am relying on memory for that. It was up a steep set of steps which served one other room.

I wil be back with our Rome apartment, one of the nicest we have found anywhere.

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Rome apartment Malva Palace:

https://www.tripadvisor.com/VacationRentalReview-g187791-d4578715-Malva_Palace-Rome_Lazio.html

This is the Tripadvisor link but it is also listed on Air B and B and has its own website as well. I chose this link because the photos load easily and it has lots of good reviews. It is a 2-bdr. But you will use the larger one on the second floor. The master bath has the best rain shower we have ever seen. Upstairs you have access to the roof decks---there are two of them. The apartment is just off the endof Ponte Sisto in Trastevere and overlooks Piazza San Giovanni Della Malva. There was a free concert ( and dancing) one square away one night, full of locals. We walked everywhere but you can catch a taxi from the stand by the bridge, or walk a few blocks to the tram that takes you to the historic center.

I would take a day from Cinque Terre and give it to Roma. It's always dodgy to me to travel a long distance for a same-day flight, but if you leave Roma at 7 or so, that might work, depending on whether you need to be at the airport two or three hours ahead of boarding.
I would consider whether you want both the Cinque Terre and the Amalfi Coast - lots to do on the Amalfi Coast, I would give it more time, but it's one of my favorite places.

Thanks for the great responses! Good things to consider. Much appreciated!

Because Liberation Day and Labor Day are so close, many Italians take the entire week for a vacation. For that reason, I advise that you book your accommodations, as soon as you get your itinerary set. I am not a fan of the CT; and ordinarily, I would say Amalfi rather than CT. However, since the drive from Tuscany to Amalfi is such a long one (6 hours?), I concur with the advice to limit your coastal time to CT. I also agree that spending the day prior to your departure in Milan is very wise. There's enough to do and plenty of opportunities for good eating to make it a happy use of a vacation day.

Add your Amalfi days to Verona and stay here.

http://www.booking.com/hotel/it/opera-relais-de-charme.html?aid=376370;label=booking-name-VuRMvKFgqAS0h89KNKa7NwSM144456195591%3Apl%3Ata%3Ap1%3Ap21%2C022%2C000%3Aac%3Aap1t1%3Aneg%3Afi%3Atiaud-146342135830%3Akwd-65526620%3Alp9022150%3Ali%3Adem%3Adm;sid=6fd3c30ae6399c21174f29e6d6a717c4;checkin=2017-06-07;checkout=2017-06-11;room1=A,A;matching_block_id=31407404_88171079_0_0_0;m_occ=2

Edit: the delux studio has a balcony.

Echoing Zoe, either the CT or AC but not both. It just takes too long to get there to make the journey worthwhile. And while you can enjoy the CT on as little as a 2-night visit, the AC deserves a longer stay. And that it's better to be as near to your departure airport as possible the night before a morning flight. Milan is certainly worthy of a day's sightseeing.

Are you locked in to the Milan flight? Flying open-jaw into Milan and out of Rome would seem to make more sense. Or out of Naples if you drop the CT and go to the AC.

If you drop the AC, then it's probably better to go from Venice to Florence. Then rent a car for Tuscany and drop it near the CT. Going Venice-CT-Florence involves backtracking, then Rome.

I like the pace; this won't be too hectic. I might opt to skip the one-nighter in Verona and just visit it on a day-trip from Venice, but it's a trade-off. It's always nice to enjoy the tourist hot-spots after the day-trippers have left.

Check the working hours of your car-rental agency on Liberation Day very carefully to be sure the pick-up won't be an issue. If you arrive to find a "Chiuso" sign on the door, you will be in quite a pickle. Even in maximally-capitalistic Washington DC a lot of the neighborhood locations have short hours around the holidays. For that matter, you can end up waiting hours here for a car on the day before Thanksgiving, especially if you don't get to the agency early in the morning. I don't know that you'll have that problem in Italy, but it's worth thinking about.

I'd skip Amalfi and add the time to Rome and Tuscany. I'd fly to Milan from Rome if you are locked into a round trip ticket home.

The Frecciarossa trains make that run in 3 hours to 3:20 for as little as 45 euros (possibly less if you buy when the tickets first go on sale). For me that would be much preferable to flying.

Car rental - in Florence, I'd bet you a gelato that they'll be closed on May 1, though the agencies at the airport may be open (Bologna airport is bigger, so more options). Or maybe switch Tuscany with Florence. I don't see much point to driving to Rome to return the car. The train from Florence is faster than driving and you won't have to deal with traffic in Rome itself. Just take the train from Florence to Naples or Salerno - depending on where you're staying in Amalfi and how you're getting there.

Your plans are all "early" to . . .. If you are early risers, that could work. But even an early train will use up most of morning, allowing time (possibly in rush hour) to get to the train station, then from the station to your hotel to drop your bags. I find that taking evening trains after a full, busy day is relaxing and maximizes my sightseeing time. I can either have a picnic dinner on the train or a late dinner after I check in to my hotel.