how about going straight to Venice from Milan, spending 3 nights there [gives you 2 days,] then on day 4 getting the train to Verona and spending the day there, getting a late train to Florence.

My only caveat is whether there is left luggage at Verona station - you don't want to traipse round with your bags all day.

Alternatively spend a night there then go onto Florence early the next morning.

jerrymel, don't worry about trying to adapt your clothing so as not to stand out. Locals will know you as tourists no matter what you wear so be comfortable. (there will be tons of other tourists wearing everything under the sun)
Really important to have footwear that you can wear all day walking around without killing your feet.

It wastes time to stay in Milan twice. You don't seem to be aware of the time needed to transport into Milan, figure out local transport to your hotel, check in (or arrange luggage storage if possible and too early for check in - not all hotels allow storage), figure transport to sites, etc.

I don't think you factored in four people trying to get ready in one bathroom in the mornings. Takes longer than you think it will as does getting to the train station, waiting on the train, etc., finding your hotel in the new location, etc. Changing city locations easily takes half a day if the train travel isn't very long.

>>> I would need Eurail but am also looking at the Italy Railpass and comparing to buying the individual tickets in advance if I set the itinerary in stone.<<<<

Rail passes are rarely cost effective for Italy. Eurail is simply a company that sells passes (as do other companies). Perhaps you are talking about their pass called a Global Pass or a one country Italy pass? Seat reservations are mandatory on the faster trains (10€ per train and rider per person) and are not included in the cost of the pass. I can't imagine a pass plus seats would be as cheap as point-to-point in Italy unless you were traveling very long distances (you would need a pass that covers at least 6-7 days for your itinerary).

The train from the airport to Milan would not be included in the pass at all. The bus is more efficient from Florence to Siena (faster and drops you much closer to the historic center) that the train. The train to Pisa from Florence is about 8€ and much cheaper to buy a single than use a day off the pass. The train from Naples to Sorrento is a private train and not included in a pass.

>>>>But we will be pretty exhausted when we arrive Verona Day 1 after a red eye flight and the train ride.<<<

Yes and you will feel more like sitting on a train to Verona watching the countryside (or napping) than attempting sightseeing tours.

I hope your plan isn't to stay in Naples and attempt to see the coastal areas from there. It's not practical.

Of your actual 15 days in Italy (I'm not counting arrival day as you will be jet lagged), you are spending 11-12 of those days traveling. You will be spending more time on getting to and from stations and on transport than actually seeing sites.

I can't imagine a pass plus seats would be as cheap as point-to-point in Italy unless you were traveling very long distances (you would need a pass that covers at least 6-7 days for your itinerary).>

What kind of point to point tickets - full-fare first class - if so I once figured the usual Milan-Venice-Rome-Milan could be cheaper with a pass even with the 10 euro added on but discounted tickets yes need several longer trips.

Generally yes vs discounted tickets a pass is hard to compete but if you want flexibility to chose which trains to hop once there it may well be.

Are you also traveling to other countries - then a Eurailpass of some kind like the France-Italy Railpass or a Eurail Select Pass might overall be a good deal but not for Italy alone - the Italy Pass is cheaper per day and there are often specials on them IME with a day free added on - often early in the spring for a limited time.

Hi everyone. Thanks to all your advice and input I was able to get everything finalized on the travel and hotel parts of this trip.

On the train, a lot or reading and finally a spreadsheet price comparison based on the Basic fare on trenitialia, which in was the most economical one with any flexibility, versus a Eurail Italy pass. I can share the details with anyone interested, but let's just say that with my kids getting Youth fares and my wife and I getting a discount for traveling together it was much, much cheaper on Eurail even considering the 10 euro per ticket fee to reserve.

In short, Basic fares for all trips came in at over 1400 euros while cumulative second class 8 day Eurail was 986 and first class 1220. I went with a 5 day First class at 906 (second class was 732). I will pay the ~25 euro per ticket from either Milan to Verona or Verona to Venice separately and have all 6 segments covered.

Finding hotels this late in the game was definitely a challenge. i managed though and think we should be fine. Most of the suggested hotels were full or too expenisive. I can provide hotel names to anyone interested.

The most difficult decision related to the itinerary was what to do on the front end. In the end we decided to make it a short train ride to Verona for two nights then continue to Venice for two nights. We will then do four nights in Florence, four in Naples (would have preferred Sorrento but no decent hotels), 3 nights in Rome and we will likely take a late train to Milan on the travel day for the night before flying out the following day.

Ambitious, I know. Lots of trains and travel days, I know. But we feel we are up to it. Our kids are older and very active, My wife and I in very good shape for 47 and 51, and we are seasoned travelers.

Now my focus will turn to the itineraries per city. I will be reading up on the boards for suggestions and welcome any you may have as well. You have all been so incredibly helpful!

I always travel with a first class Eurailpass in Italy and never ever have had any trouble getting mandated reservations as I go along - you can make them all in other Italian stations too and IME first class for the trip of a lifetime and especially with luggage is a smart decision - apply the same criteria to train travel as you do to hotels and restaurants - starvation budget go discounted 2nd class tickets - that are train-specific and can't be changed. The pass gives you flexibility - if you miss the train you book with a pass if you miss the train you lose only the 10 euro booking fee.