Type of Mask and are they really mandatory?

You can get away with any mask on public transportation if they are still mandatory when you get there. The official recorded announcements on the trains recommend the FFP2. At some stations the government hands out those for free.
https://www.trenitalia.com/en/info_contacts/for-a-safe-journey-on-board.html

And if you want to better your chances of not testing positive and having to stay in quarantine wear the mask in crowded situations

Depends on why you are wearing the mask? Simple compliance with not much protection, or to be safe yourself and for others.

Why would you choose to wear a less effective mask?

For now the FFPE2/N95 is what is required on public transportation and in theaters.
The Italian government is however likely to loft any mask requirement on June 15.
Nevertheless, since the virus is still going around and tens of thousands of new positives are registered daily in Italy, I wouldn’t take chances to ruin my vacation by getting sick or being stuck there unable to come home since the US Government still requires travelers to test negative before boarding a plane back to the US. If you want to increase the chances of not getting infected, wear the proper mask in any crowded situation, such as public transportation or any indoor gathering. I plan to eat outdoors too when I go.

Yes...still required on plane (surgical was ok on Lufthansa) Al Italia agent asked to see my mask to make sure I had an N95. Strict on bus, train all public transportation in Italy.

We have been in Venice, Florence, Cinque Terre and Rome, plus quick days trips to Pisa and Pompeii, these last couple of weeks. We flew in on Air Canada. Here's our mask experience.

Air Canada enforced masks, including telling people to cover their noses and announcing food service is over and time to mask. Surgical masks were fine. They provided kits with surgical mask.

Vaporetti in Venice: they enforced masks, but not type of mask. The always checked that you had a mask with you if it wasn't already on and they will turn you away if you didn't have a mask.

People wore masks on trains and they kept running announcements about it being mandatory. All but one time, surgical mask was fine. The one time, strangely, the employee checked tickets and didn't say anything about the surgical mask and then woke us up later to tell us to change masks. This was on Trenitalia. In the train stations, it was mixed between people wearing masks and not.

Rome Metro and bus: everyone wore masks but we didn't notice any enforcement.

Rome taxi: there was a plastic barrier between front and back seats. We had one driver who didn't wear a mask and one who did. We didn't wear them in the back seat and no one said anything.

Circumvesuviana to Pompeii: only public transportation where some people didn't wear masks.

None in our group of 5 had a cloth mask and I didn't notice anyone with cloth mask so can't say how those would be treated. Also, common to see people having them on but not covering their nose, stuff like that.

St Mark's Basilica was requiring masks (surgical fine) but Doge's Palace was not. Not required at Uffizi, Accademia, climbing the Duomo in Florence, nor for climbing Tower of Pisa. Most of the things we've done in Rome are outdoors, so I don't have a good report. We bring ours everywhere and just follow what everyone else is doing. Tested negative this morning, just in time for the last day that it's required...cost 95 euro for 5 of us. Great timing for us! Oh well.

When in a tightly enclosed space they are mandatory. We were on a cable car in Taormina, Sicily and masking was enforced. We couldn’t even get into the area where the ticket machine was located without one. It was also enforced on the elevator up to the dome of St. Peter’s in Rome. Those were the only incidences where we were on any kind of public transport that I can recall.

We are now in Rome and have been in Italy the past three weeks.
For trains: surgical, ffp2 and kn95 were accepted. We’ve seen some enforcement for non-wearers.
From vaporettos in Venice, mask needed for onboarding. Same above forms were accepted.
We’ve also had about 20 taxi rides and we used an ffp2 or kn95 each time. About 5 of the taxi drivers were initially masked and about 5 put one on when they saw we were masked….The other 10 did not.

We visited the Vatican Museums today, June 10 and we were surprised to see about 95% non-mask wearing among visitors in the usual crowded conditions. All of the staff wore masks and about 2/3 covered their nose and mouth.

We have been on 3 trains the past week in Italy. ALL of them required a FPP2 masks. If you had a surgical masks, they had you go to the bar and buy a FPP2 masks.

Yes- just two days ago we saw an Italian couple booted off for not having proper masks. They are sold everywhere- including at stations and pharmacies and they are inexpensive- 5EU for 5- 10 FFP2 masks. They do allow kn95, n95, and FFP3 instead of FFP2 - but it must be quality medical grade.

At the ferry terminal in Como, there are some entrepreneurs doing a brisk business in FF2 masks as nobody was allowed on the ferry without one.

I have been in Italy since June 1. The KN95 type mask is required on public transportation - trains, trams, buses, etc.. I have seen a few blue medical masks but no, cloth masks are not a substitute.

And also the same requirement for indoor concerts & museums.

For reference, I haven’t seen any of the KN95 ones worn that have the elastic straps completely over the head; everyone’s wrap around the ears. There are white, black and some solid colors that are stamped “made in Italy”.

I was at another concert last night, and they not only required the KN95 type, but they made us each say we would keep it on while we were inside. One guy (there’s always one!) tried to wear it over his chin & mouth, and one of the workers made him wear it correctly to be able to stay for the concert.

I rode a crowded vaporetto this morning and looked around. The majority were wearing the KN95 type - just a couple of blue medical masks. And everyone was fully wearing them.