Eurail Pass

Depends on what the 7 cities are. Care to share?

Italian train tickets are not generally very expensive. Fares on the fast trains vary, starting out quite inexpensive and gradually increasing as other folks buy the cheapest tickets, but even so, you may not need to pay as much as you anticipate for your tickets. Since Italian rail passes don't usually pay off for visitors, it would be good to list the trips you plan to take so folks here can comment on the probable utility of a pass.

What's not always clear in discussions of rail passes is that in some countries (and Italy is one of them), rail pass holders have to buy seat reservations when they take fast (express) trains. Those reservations cost about $10 per train, I think. If you buy individual tickets instead, the reservation fee is already included in the price you pay, making the rail pass even less likely to pay off.

Yet another complication in Italy is the existence of two companies operating express trains, only one of which also operates standard trains serving smaller cities. Rail passes are good only on Trenitalia trains (serving cities and towns of all sizes). They cannot be used on Italo trains.

It would be helpful to know when you plan to take the trip, since that may affect your ability to buy bargain-priced tickets on express trains.

I doubt an Eurail Pass will be useful in Italy.

• Local trains are cheap. Just buy tickets at the station.
• Long distance trains require reservations. So you will have to queue up at the ticket office, in stead of just being able to buy your ticket using your phone, or a ticket vending machine.

And the Eurail Pass is not valid on the private operator Italo, limiting your options.

But tell us what your plan is.

We are thinking of going to 7 cities...and I am wondering if we need a 7 day pass?

you may be thinking that every train you take requires a day of pass use. You can use as many trains each day as you want (on covered lines, and after buying the reservation for every leg of not slow trains) for 7 whole days.

The best thing is if you'd share which cities and in which order (and how soon) you plan to travel. The more info you give us the better answers you'll get - otherwise we are shooting in the dark.

Thank you all for your kind responses......appreciate the thoroughness in your responses as well

Itinerary: Milan---> Padua----> Venice--->Florence--->Rome--->Naples

(Extra trip would be Lake Como if we can squish it in for a few days)

are you flying out of Naples or returning to either Rome or Milan?

Padua to Venice is a very cheap 4.80 EUR on a regionale veloce train. No need to waste a pass-day for that. Just as fast as a Freccia train with no reservation fee.
Milan to Lake Como is a cheap regional ticket as well.

You haven't given us any travel dates, so I arbitrarily chose May 15 for the purpose of my rail-fare research.

For each leg of your trip I'm showing two fares found on the Trenitalia website for tickets purchased today. The low fare is for travel on May 15 (though prices can vary from train to train); the high fare is for travel tomorrow. As you can see, they practically give the tickets away if you buy them several months ahead of time, but you'll usually pay several times more for express-train (Freccia) tickets if you buy at the last minute. Even so, the last-minute ticket prices are not exorbitant in Italy.

Milan to Padua: €10.90 to €47
Padua to Venice: €4.80 every day (a regional train with fixed fare)
Venice to Florence: €18.90 to €59
Florence to Rome: €12.90 to €55
Rome to Naples: €11.90 to €52

Those fares include the seat-reservation fee that's mandatory on all the trips except Padua-Venice.

You can research fares on your actual planned travel dates here:

Trenitalia

Italo (Don't use Italo for Padua-Venice.)

On any given trip, Trenitalia or Italo might be a bit cheaper than the other. Since Italo runs only express trains, you don't want to use it for the short hop from Padua and Venice; you'd be paying for speed but not really getting it.

On the Trenitalia website (but not on the Italo website) you must use Italian station names. These are the ones you need for the itinerary you've laid out:

Milano (Tutte le Stazioni) -- that means "all stations"
Padova
Venezia S. Lucia
Firenze S. M. Novella
Roma (Tutte le Stazioni)
Napoli (Tutte le Stazioni)

Once you have your hotels pinned down, you can consider whether you want to try to find a train departing from or arriving at a particular station. Each express train normally stops only at one station in a city.

Thank you so much for the help----I appreciate the thoroughness of the responses.
Excited to travel in Italy by train in June!

Wow! Your responses have been so detailed and helpful that I am going to chime in with my itinerary and see what you suggest for rail travel.

Is the Eurail Rail Planner app helpful?

Thu May 23 arrive Milano Malpensa →Bologna
Sun May 26 Bologna→Firenze
Wed May 29 Firenze→Le Cinque Terre (Vernazza)
Sat June 1 Le Cinque Terre→Genova
Tue June 4 Genova→Stresa
Sat June 8 Stresa→Milano
Tue June 11 Milano→Malpensa

Thank you for any help you can lend. Researching rail options can be a bit overwhelming and stressful

Just go to https://www.trenitalia.com/en.html to get the prices for your dates. If your date is after June 8, it may not be showing up yet on the schedule.
The Malpensa Express train is not valid with the Eurail Pass.

You're not covering a lot of miles there, so I think a Eurail Pass would be a big waste of money. As previously noted, you can save considerable money on tickets for express trains by making those purchases early.

You might also download the Trenitalia app and keep an eye out for sales. They have some incredible sales—in the app and on the website. Also, the app is very useful for paying and for checking in. And it has an English option. (One warning: if you are waiting to check in until you get to the train station, make certain you have cellular coverage.)