My question is should the plan be Venice, (maybe insert 2 nights in Florence), Rome, Naples then Vienna or in a different order?>

Depends how you go to Vienna from Italy - if flying from Naples fine but you can take a gorgeously scenic daytime train Venice to Vienna or an overnight Hotel Train - those would be much longer from other places.

I'd say end in Venice and take day or night train to Vienna. Day train see some lovely lovely scenery.

and, I should add we will not drive more than likely but take the train

Thanks for all your advice. I was hooked on the idea of Vienna being our last leg but for no significant reason. So, I have decided Vienna first, then train to Venice, Florence, Sorrento and then back to Rome to fly home. We have 6/1-18 so that should be enough time to get a good visit in at each destination.

If Rome will not include significant touring, it would be easier to fly home from Naples with a change of planes in Rome, and would gain a non-travel day.

AJPeabody - we are using miles so Rome is the better choice for this purpose.

Can you use miles to fly into Venice or Milan?
Did you go to any of the smaller islands when you were in Venice?

I would arrange the itinerary this way.
Fly into Venice, 2 or 3 nts
Train to Rome, 4 or 5 nts (include Ostia Antica as a day trip)
Train to Sorrento, minimum 4 nts,
(Ferry down the coast to Positano and Amalfi, ferry to Capri for a day,
train to Pompeii).*
Train to Naples, do underground tour (if your son would enjoy it) and archeological museum.**
Fly to Vienna from Naples.

*You could visit Pompeii (or Herculaneum) on way to Naples. Drop luggage at entrance storage at Pompeii or Herculaneum.

**Fly to Vienna in the evening or spend a night and go the next morning.

The Naples airport is small and not far from city center, quick and easy to get to and easy to navigate.

With an 11 year old, I like Sorrento, especially if you get a nice hotel with a pool and great view. I highly recommend Hotel Minerva because the pool is on their beautiful terrace. Your son could swim while you sit with a drink and enjoy sunset over the bay of Naples.

Sassafrass, thank you! this is a great plan. While I think our son would love the train from Venice to Vienna it is not a deal breaker to cut that step out.

My opinion on where to stay on the Amalfi Coast is different. But it will give you another perspective. I always try to stay in the most scenic location as opposed to the most convenient base. I visited Positano and Capri on separate trips with my daughter ( 3 and 4 years old at the time). She is little mountain goat and had a lot of fun with the stairs, jumping, skipping, and swimming in the sea. The location added to her enjoyment of the trip. Our hiking trips became "exploration" trips.

As for me, what can I say, except I need a breathtaking view of the Mediterranean blue at every street corner, from every window if possible...

and, I should add we will not drive more than likely but take the train>

Great decision for your itinerary- cities and Amalfi needs no cars nor is conducive to cars.

ToujoursVoyager, I am in agreement with you. We will be staying in Positano as I just cannot imagine staying anywhere else!

As for me, what can I say, except I need a breathtaking view of the Mediterranean blue at every street corner, from every window if possible...>

this is why Sorrento sucks for places with views from all over - Positano IME since it literally spills down to the sea is perfect - other towns like Amalfi do not.

http://www.oebb.at/en/angebote-ermae...n/wien-venedig

Details on hotel night train Venice to Vienna - again I took overnight trains with my son when he was that age and it was rather romantic for him - unique experience to consider. 69 euros p.p. in private triple including train fare and sleeping berth.