my wife and will be traveling to italy for our first time next month. a couple questions:

1. if we are traveling from city to city via eurorail, trenitalia and/or .italo - would you advise booking our tickets in advance? i'd prefer to just buy on site to keep things flexible.

2. i need an unlimited pre-paid data sim for 7 days. what would be the best carrier for this? any idea on approximate cost?

thanks so much in advance for your time =)

Did you see the board for European Rail Travel? I'm sure your first question has been asked by others. You will pay more if you wait, but at one month out, it may already not matter.
My family traveled to Rome, Florence and Venice this past June; we kept an eye out for the release of the schedule, so we could secure the cheapest fares.
We rode Trenitalia from Rome to Florence for about $25 per person (76 euros for 4 of us) and Italo from Florence to Venice for about $27 pp (84 euros for 4).
While our daily activities weren't always too structured, we had arranged hotels in advance so it made sense to buy train tickets in advance too.
Have a great trip!

italy is one country where the train tickets are cheap enough that you don't really need a pass. Just buy tickets on trenitalia

I don't think trains in Italy are that cheap. Rome to Naples, Milan to Bologna, wherever I go I seem to cough up 60-90E per ticket. I usually buy at the station because my plans usually have to be flexible.

That said, it is worth looking at the Trenitalia website to pre-purchase when possible. Yesterday, two of us traveled from Lamezia to Rome on a 2 for 1 Trenitalia 96E special that was only visible on their website. You couldn't purchase it at the train station. The week before we went from Rome to Lamezia without awareness of the special, and paid 96E each.

Don't know what part of Italy you will be traveling to, but in general, lines at the ticket station can be long and slow. You should use the machines to buy your ticket, but you generally need a credit card with a pin number. Some machines take cash (euros), some don't. I've seen situations where there is no salesperson at the station, just a machine, the machine would not accept cash, and the person didn't have a pin number for their credit card. That can be bad.

Depending on which train you are on, local or not, validate your ticket by inserting it into a yellow machine before boarding, or else face up to a 200E fine if caught on board. A ticket with a date and assigned seat doesn't need to be validated, just local trains without an assigned seat.

In some cities if you are using the machine to buy a ticket at the station, someone will come over and start helping you, like it or not. Tell them you don't need any help because when they finish they will expect a tip and give you bad looks if you don't cough it up (note, I've only seen this in Naples, where someone also may also offer to help you bring your luggage down off the train then start giving you menacing looks if you don't give a tip.).

The WIND network "All Inclusive" package currently offers unlimited Internet access for �7 per month. You'll have to pay �5 for the SIM card and probably �10 for the "All Inclusive" package (as I think I'm right in saying that they only do 'top ups' in units of �5 � so you may be left with �3 credit.) Not a bad deal for �15.

My mother-in-law, (who is visiting Italy from the States) currently has this package on her Samsung Galaxy Note and my 'other half' has it on her iPhone 4S. In both cases it's working very well.

You can compare the price of the discounted tickets and the full-priced tickets on the websites of trenitalia and italo, and decide if you want to pre-book at today's prices, which will increase, or if you want to buy at the train station. I'd do the first, rather than the second.

so it seems the consensus if to buy tickets ahead online.

considering my itinerary, is there a preference of one train over another? i don't mind paying a bit more for comfort just as long as price is still reasonable. i've read up on other threads and don't really get the upside of one train line over another.

milan to venice
venice to florence
florence to rome

i appreciate the patience and thanks so much for all your input =)

this is perfect! any idea if the Wind network has a retail shop at the Milan airport?

There is no WIND store at Milan Malpensa T1 and almost definitely not one at T2. I'm not sure about Milan Linate, although I was there recently and certainly don't recall having seen one.

As you're enquiring about train travel, I'd guess that you're planning to travel from Milano Centrale station early-on in you tour. If this is the case, I can confirm that there is a WIND store at Milano Centrale station on the lower ground level, a short distance from the Metro entry barriers.

Happy travels.

Last time I checked, trenitalia had 5 classes of service on Frecciarossa trains (3 classes, 2 service levels in economy and business), and .italo has 3 classes as well. Both have free wifi, which in my experience works a bit better on .italo. Trenitalia has more trains.

I'd say it's a wash. Time and price should be your guide to buying tickets. Sometimes business class might be cheaper than economy class, or close to it. For a marginal difference, I would upgrade to a better seat.

Absolutely. We used both, and while we liked the Trenitalia ride better than Italo, it probably had something to do with the fact that Italo ran 90 minutes late and our car had a large group of lively 10-year-old boys running around.

A few days after our journey, Italo sent an email which said that we were due a 25% refund of the fare because of the delay, either in the form of a credit toward a future ticket, or a wire transfer to a bank account. Since we have no current plans to return to Italy, I called them when we returned home, and the wire transfer took about a month. ^

PS Of course if your cellphone is 'locked' you will need to get it 'unlocked' in order to use the WIND (or any other Italian network's SIM card). My mother-in-law has a contract with AT&T. She asked them for the unlock code, which they provided free of charge at the store.

Advance train tickets bought on the website are much cheaper than buying last minute full fare tickets on the platform. Check the website prices and promos. If you have time they are pretty cheap

I bought a Wind sim for my iphone 5 at Termini. They told me it would take 2 hours for it tone activated. I had all sort of troubles getting it to work though. I had to change the APN, and my iphone get insisted I needed to deactivate it. My problems were this:
When I landed I had turned cellular data off
Inserting the wind sim in my iphone asked to unlock the sim and for activation (is this a new ios 7 feature?)
With data off I was unable to activate the iphone.

Solution: before removing your old sim make sure your cellular data is on, remove old sim, insert new sim but do not unlock it yet. Go to settings and change APN. Then unlock the sim and proceed with activation. It took me a couple hours to figure that out.

FDW
Cellular data was off