SIM card at Milan airport or in cinque terre

There is a small foreign exchange desk at the baggage carousel area of malpensa. They sell Vodafone Holiday SIM card. It costs €30 and u get 300 mins, 300 txt a and 2gb of data. The txt and mins can be to the U.S Or dozens of countries. A way better deal then verizon (IMO).

But your iPhone must be "unlocked" in order for the SIM to work. I don't think VZ will let unlock a phone that is under contract.

We used an iPhone 4S that was and old phone of ours and it worked super.

Try to get your SIM card in Milan. When in France last autumn, I had difficulty locating a nano SIM. None available at CDG. Arrived in Strasbourg, went to three cell phone stores. No luck. Finally tried one of those shops that offers phone and email services for immigrants. Though they only had a micro SIM, they also had a punch with a die that cut it to size. Had no problems with it.

whodat, do they speak English, and did they install the sim and set it up for you?

The lady at the FX desk spoke broken English. She did give out written instructions in English (but if I recall they too were not a model of clarity).

The mail thing she told me (and the main thing the written instructions said) was to not insert the SIM for 3 hours after purchase. I think the 3 hour delay has to do w the fact that, while she took a photocopy of my passport she did not forward it immediately to Vodafone. I suspect she sends them in batches. I was fine with it as I was in a rush to catch the malpensa express (but I'd be lying if I said I wasn't nervous that it wasn't gonna work).

I asked the sales lady for a paper clip (since I forgot to pack one) to open the SIM card door. I was comfortable doing on my own. Those nervous about it should simply try opening theirs on their own.

FYI. The SIM was a combo (where it fit two sizes).

There is a MediaWorld electronic super store inside the station at Milano Centrale. They sell everything for your telephone needs. They can insert the SIM card for you. But you can also insert it yourself, it's very simple. Actually you should learn how to do it, because eventually you will have to put your American SIM card back in it. You need a little tool to remove the casing. However a paper clip works just as well. All you have to do is insert that tool (paper clip) in the little hole and the casing will pop out. There are plenty of tutorials on YouTube. Try at home before you leave.

This is how you do it with the Apple tool:
http://www.jakartanotebook.com/images/products/33/9/2211/1/sim-card-tray-holder-eject-pin-key-tool-for-iphone-4-1.jpg
https://support.apple.com/en-vn/HT201337
This is how to do it with the cheaper paper clip:
http://images.mentalfloss.com/sites/default/files/iphone_sim_removal_tool_6.jpg
http://www.maclife.com/files/imagecache/futureus_imagegallery_fullsize/gallery/0118_sim_3_1024_0.jpg

It is not true that you have to wait 3 hours to insert the SIM because of the passport copy. That must be a joke. I buy 2 Vodafone Holiday SIMs a year and always insert it on the spot. What is true is that you must wait for the activation text message (a series of welcome messages telling you the services that are activated) from Vodafone before you use the phone. The welcome message is in English. That message signifies that your plan is active. If you use the phone before that message, before the data plan is activated, you will be depleting the credit in the card. It takes a few hours before you receive that series of texts, probably less than 3 hours.

Don't wait to buy the SIM at the Cinque Terre, otherwise you might have to go to La Spezia. I don't think they have telephone stores in any of the five tiny villages.

Is it usual and customary to require a passport photocopy to purchase a SiIM card?

Jean, yes it is usual and customary to prove your identity

You will need your passport. The store will make the photocopy and also will calculate your codice fiscale (tax code) online. I checked last summer and it's still required.
You can also calculate your own codice fiscale on the website below.
For place of birth use STATI UNITI.
Your name should be as it appears in your passport. The first name should include the middle name if the passport has one.
http://zip-codes.nonsolocap.it/codice-fiscale/