Italyrailpass vs point to pint tickets for Rome-florence-Venice-Milan

There is no long-distance train departing Malpensa and this airport train is not covered by passes on either day 1 or 7 of your plan. Be sure to choose the shuttle train with the destination of Milano Centrale station (not Cadorna), since that's where you catch most trains to Rome. You can buy the tickets upon arrival for about $100 per person in the cheapest class of service. Tickets booked from home are not usable if you miss the scheduled train.

This is an example of a time when a Eurail Italy Pass offers you both a moderate total price and no worry about missing the booked train. You have to have the pass activated in Milan (probably fastest at the travel agency that's inside the train station or one in the airport) and can buy a seat reservation at the same time. Trips 1 and 2 are each a $100 value at full-fare 2nd class.

Since you can currently get a pass for 6 travel days in a month for $206 per adult in 2nd class or $256 in 1st, I would choose either of those. If there are kids under 12 in the family group, then they can be added to the pass for free. Seat reservations for the 6 trains that require reservations will add $72/€60 per person. Trains between Florence and Pisa don't generally take reservations, so you can just hop on those. The $206 price is based on the current extra-day special and those passes are not refundable or changeable once purchased.

If you know exactly when you will travel, price out the point-to-point tickets on Trenitalia.com. It will show you all trains and all prices. If you can commit to a specific train you may save money with the nonrefundable, nonchangeable supereconomy fares. Rail passes are often not the most economical option in Italy.

Thank you Laura and Zoe.
We will be carrying checkin luggages(atleast 1 big rollon). Was wondering how safe it is to travel in second class with kids?

PE, we ONLY travel 2nd-class carriages on Italian trains and have never had a problem. They're comfortable enough not to need to spend extra for more expensive tickets.

Sorry PE, but why there should be a difference in safety between first and second class? There are automatic doors that anybody can open to pass from one car to another.

I mean that, If you are worried, you should take the exact same precautions in first you'd take in second class.

I read somewhere that second class might be crowded(not sure if they let people in without seats like in Metros ) , hence was worried about pickpocketers..

Pickpockets on long distance trains? They wouldn't know where to run away if caught.
If you are worried about pickpockets keep an arm around your bag when gettin on/off subway cars and buses.

Looking at your itinerary, the Circumvesuviana overground metro that connects Naples, Pompeii and Sorrento should be the only train where you'll probably have to face this kind of problems. On the other hand, if you are aware of the problem you'll take obvious precautions, so they'll look for easier targets and you won't face anything... !

Since Sorrento is not in your plans, you don't have to worry about that, but Dario's advice is sound nonetheless. I never travel first-class unless all the cheap super-economy tickets are sold out, and the cheapest first-class ticket is usually within a few euro of the second-class ticket.

PE is going from Rome to Pompeii (trip 2): they'll have to get off at Naples' Centrale station, walk to the underground level and get on the Circumvesuviana train headed to Sorrento. The line to Sorrento is the only one that calls at Pompeii just in front of the archaeological site main entrance.

Like on a metro network there are more Curcumvesuviana lines with different final destinations. They must take the Naples - Sorrento one to get to Pompeii.

The longer, reserved trains on your list don't allow extra travelers to fill up the aisles and they make very few stops. However, crowding could be possible on a regional train between Florence and Pisa and is almost guaranteed on the local Circumvesuviana line between Naples and Pompei (which doesn't have 1st class and is not covered by rail passes).

Thanks everyone!

For a random day in May, Trenitalia shows base fares of €46 from Milano to Roma.

My one comment is to re-consider the one large checked roll-on. How big a roll on are you talking about? You will need to lug this thing where ever you go including up and down stairs at railway stations and up and down steps onto and off of trains.

I am taking atleast one checkin size rollon with us..