June 2012. Just spent a few days in Italy. Figured I'd write some tips down for others, especially about Kosher food and Jewish stuff.
ROME:
There is no eruv in Rome.
It's fun to walk around on Shabbos, but keep in mind it's really hot during the summer months, and hard to go long without water.
There are lots of kosher restaurants in Rome. There are also lots of shuls to choose from! Some have a kiddush after davening on Shabbos day.
A great website is: http://jewishitaly.org/city.asp?City=Rome
They have all the current information there.
For Shabbos, we ordered meals from Meir Babani - http://jewishitaly.org/detail.asp?ID=327
We were very happy with it - it was very good and had some Italian style dishes along with traditional chicken, schnitzel, salmon and others. What was nice is that he offers delivery included, and also plastic-ware and candles. 35 euro a meal per person. (so 2 ppl for Fri night and Shabbos lunch = 140 euro). Worth it! We found some of the other take out food so "Roman" (Italian) that we just weren't used to it and it wasn't good...
In terms of Glatt meat - you need to check if the restaurant you are going to serves Glatt meat - some have it available upon request (and that caterer above uses Glatt).
Cholov Yisroel - some are, some are not, so check first if applicable. Yotvata is, and is delicious! http://jewishitaly.org/detail.asp?ID=108 (its in the ghetto but not on the main strip).
We enjoyed the 3 "Ba'ghetto" restaurants!
Do a tour with a Jewish tour guide - we used David Walden and really enjoyed. There's lots of Jewish history in Rome!
Amalfi Coast (Sorrento, Possitano, Amalfi)
There's nothing kosher there, but we ordered food from a lady who made it in a kosher home and she delivered it to our hotel. Half was great (the pasta stuff, salad), half was just not our style, but still was good to have. Also, would have been better if she had pre-double-wrapped it and labeled it with what was inside; would have been less confusing for the kitchen staff.
You could also bring food from the bigger cities of course, just depends how long you're going for.
Milan
Has some kosher there, didn't get to it, but heard about it. Seems to have many options. http://jewishitaly.org/city.asp?City=Milan
Stresa
Has a kosher caterer. (There are Pesach programs run there on Pesach - likely same caterer: http://jewishitaly.org/detail.asp?ID=292 )
The website: jewishitaly.org is really great - run by Chabad.
Found out after that there may be a "kosher list" for Italy! Too late but if you google it, you get this (didn't get to verify any of it yet)
http://www.italykosherunion.it/Kosher%20food%20list-en.html
http://www.italykosherunion.it/
Comment on this to help others travelling there!