Italy itinerary questions, and seeking suggestions

I’d probably do Milan first then Lake Como

You can drop the car in Orvieto and train to Naples (hertz)
There is a direct IC train leaves at 10:38

Since you are leaving from Amalfi take the ferry to Salerno then direct train to Rome - it’s a lovely ferry ride

No interest in Paestum?

For the Lake Como question, what time do you land in Milan? It's an hour from the airport to the central Milan train station, then an hour train to Lake Como. If you land later in the day, you have fewer train options to Lake Como, as waiting between connections eats up time.

Where in Lake Como are you staying? My preference is to give the area another day, as it's so beautiful and relaxing.

Safe travels!

Pat I think it will likely be an overnight flight that lands in Milan in the early morning (hopefully catch some sleep on the way).
ChristineH I’m definitely interested in paestum but I just don’t think we have time to squeeze it in :-(

Guess it depends on what you want to see/do in Milan
If just to take a look at Duomo and wander around that would be an OK jet lag day

Yes, you’d have to give up something somewhere to stay a night or 2 in Salerno to visit Paestum
We did enjoy Salerno very much

You do have a lot of one nighters
Siena- make sure you pick a hotel with easy access parking or stay outside the walls

We liked Assisi a lot as well but that might be the one location you could consider dropping?

You could stay in Naples OR Sorrento to combine those one nighters

Milan we’d like to do the duomo and the last supper and possibly sforzesco castle depending on how we feel and time.

I’m definitely most unsure about the Siena, Assisi, Orvieto part of the trip. They all seem interesting and they were a part of Rick Steve’s sample itinerary and we wanted to enjoy some of the countryside.

I’m not excited about the one nighters in the south but I thought it would be less total transit time if we just kept moving in the same direction instead of going back and forth to a home base.

Have you bought your plane tickets? If not consider flying into Venice or Naples and out the other.

Should we go straight to lake como from the airport and visit Milan for a day or leave our Milan day as the first day?

What’s great about Milan is you can take a day trip to Varenna (1h 15m by direct train). While in Varenna, hop on the 15-minute ferry to Bellagio and have lunch. Sleep in Milan not Lake Como. Furthermore, it will be way more convenient so take a direct train from Milan than Varenna to Venice (2h 30m).
A train from Venice to Vernazza takes a full day and requires multiple connections. How many nights will you be in IT? If you’re flying into Milan and out of Rome, perhaps you should cut Venice and the south of Rome. Assume you’ll return when you can fly from Venice to Naples and continue on to Sicily which is also well worth seeing.

I’m not excited about the one nighters in the south but I thought it would be less total transit time if we just kept moving in the same direction instead of going back and forth to a home base.

This may be true, but don’t forget to account for the significant cumulative time you are going to spend instead checking out of and into a new hotel every day. I would bet that eats away any “saved” transit time. Plus it’s just exhausting having to do that day after day (having to negotiate everything new every single day).

Many of us here find the RS tours/ itineraries too fast paced
Too many 1 nighters is exhausting

I’d drop Civita and Assisi
Spend 2 nights in Orvieto or Siena
If you add a night to Florence you can day trip easily to Siena

Stay in Sorrento for 3 nights-visit Pompeii and Capri from there (Mondo Guides are excellent www.sharedtours.com- search this forum for lots of happy customer reviews)
Enjoy the evenings in Sorrento, it is delightful great restaurants etc
Then move to Amalfi for 2 nights

Not sure how that frees up itinerary but I think you’ll enjoy your trip more if you slow down a bit

Piano, piano!

David-
Since your subject line does say you want suggestions I’m going to go with that. I remember well planning our first trip to Italy- we only had 17 nights, so a whole week less than you have- how lucky you are!
I got the books, the maps, I looked at all the suggested itineraries and said “I want to go to all of those places” then the further along I got in planning- with some awesome help from this forum- I realized that was simply not practical. Not even sure it would have been practical if I had 23 nights as you do. (Count your trip in NIGHTS, a 2 night stay really means just 1.5 days to enjoy whatever location you are in)
This is a vacation not a Death March.

I somehow missed that you have Venice in your plan. Wonderful. But you also have 4 “water/coastal” locations- Venice, Como, CT and Amalfi. Pick 2 or possibly 3. I don’t know what is more important to you so research CT- make sure you know how crowded it might be, what will you do if the weather is lousy? research Como- is there enough to do there to warrant 2 nights plus the nights in Milan. Is Milan a bigger priority than Venice? The sights you listed in Milan probably need 2 nights.

Venice is a fantastic entry to Italy and a great place to get over jet lag. Easier to fly IN to than out of. If you can start your trip there you won’t regret it. Venice is unique, there is no other place in the world like it. Give it the 3 nights it deserves. Minimum.

Florence needs a minimum of 3 nights- hopefully not over a Monday because many museums are closed that day. Add 1 night for every day trip you take from Florence.
We’ve never bothered with Pisa. Too many other places more interesting.

You are renting a car but not really using it where it benefits you most. Tuscany is where you want the car. You can visit Montepulciano, Pienza, Montalcino with a car on your own- better yet- stay in Montepulciano.

Sorrento/Amalfi area has so much to do. We spent 9 nights in the area and are returning this Sept for 4 more nights- mainly just to chill. You’ll get a bit of everything there- views, water, hiking, relaxing, great food, fun shopping and wandering.
Pompeii is huge and exhausting- give it a day. Capri is a day. Naples is a day. All super easy day trips.
Positano was a half day for us. Not impressed. Ravello is lovely- give it a full day so you have time to walk out to Villa Cimbrone. Fabulous iconic Amalfi views.

This was our first trip. It was the perfect first trip. For us.

Venice 3 nights
Florence 3 nights
Picked up car and drove to Siena along the Chianti Road
Siena 2 nights- no day trips- just stayed put in town
Montepulciano 2 nights- day tripped around Tuscany/Val D’Orcia- can not wait to go back but car rental rates are outrageous this year ;)
Drove to
Assisi- 2 nights- day tripped to Spello on 2nd day- lovely little village, nobody there but us.

Then we dropped the car in Spoleto and trained to Rome for the last 5 nights. You can never have enough nights in Rome. Seriously.
We started our 2nd trip in Rome and will end this upcoming trip in Rome- we love it.

We really wanted to go to Orvieto but had to cut that. We are finally going to Orvieto on our next trip. It’s not going anywhere. Assume you will return.
I am not at all sure what the attraction of Civita di Bagnoreggio is to be honest.

We are actually flying into Milan this time but not spending any time there. Too complicated right now to score Last Supper tix- we’ll save it for “next trip”. Just so happened that was our best choice for a flight and at the time a COVID tested-no longer need that. We’ll head to Stresa on arrival and use that quieter place to get over jet lag.

cont...
Do your research. Realize you don’t have to see every single town and sight listed in RS guide books. And not to make it more complicated but Bologna and the Emilia-Reggiano region has a lot to offer as well- not even mentioned in RS guides. Especially since you mentioned being a “travel for food kind of guy”

Try to avoid too many 1-2 night stays.

Even if you are “busy travelers”- leave the busy-ness for your time in each town/location not the getting to and fro.

The folowing tips imply that you

• can fly into Venice and out of Naples
• in the Cinque Terre you are open to stay in Monterosso and not in Vernazza
• you understand that most Italians try not to drive in Naples.

So, if I were you I would

1. fly into Venice and stay there not less than 2 nights
2. take a direct hs train from Venezia S. Lucia to Milano Centrale
3. spend two nights in Milan, on day 2 make a day trip to the Lake Como (train from Milano Cadorna to Vernazza, ferry to Bellagio, ferry to Como, train back to Milano Centrale)
4. on the 3rd day in Milan, take a direct Intercity train to Monterosso in the early morning. Intercity=no changes & reserved seats all the way to Monterosso.
5. Stay in Monterosso as long as you want
6. Train to Florence (if there is a direct train from the Cinque Terre to Florence I bet it departs from Monterosso)
7. Four or five nights in Florence with a day trip to Pisa and/or Lucca
8. Bus or Train to Siena (bus is better if you are staying on the top of the hill)
9. Sleep and pick the car in Siena
10. Drive to Assisi, Civita di Bagnoregio (?) and Orvieto. Change hotel every day if you really want to.
11. Drop the car in Orvieto (this means your choice of rental companies will be restricted to those with an office in Orvieto)
12. Sleep in Orvieto then take a direct Regional train to Rome
13. Stay in Rome as long as you want, then take a Direct hs train from Roma Termini station to Salerno
14. In Salerno take a ferry to either Positano or Amalfi and spend more time on the actual Amalfi Coast (Sorrento is nice but it is not on the Amalfi Coast). Visit Ravello by bus
15. Private driver to Naples via Pompeii (drivers are used to wait a couple of hours out of the gates)
16. stay 3 nights in Naples. Make a day trip to Capri.
17. Take an official taxi to Naples airport and fly home.

It still seems the "Bataan Death March 2022 Edition", but at least you would minimise the time on trains and backtracking. Frankly I'd never try to visit both the Cinque Terre and the Amalfi Coast.

Actually, "drive to X" means: "drive to X, avoid the local ZTL, find a parking spot, pay for it".