Hi King, welcome to the forum. Lots of very friendly and helpful people here.
I just got back from a five day trip from Rome and will be submitting a lengthier thread about what I found there. Headed to Florence in a few weeks and will also update the forum when I return.
Long story short, there is really only one word that sums up tobacco in Italy--Toscano. While cigarettes are consumed en masse, the second most popular choice were these very cool and unique dark fired Kentucky cigars. They have a multitude of different flavors and strengths and I brought a ton of them back. Very inexpensive as well--my favorites were the Garibaldis and the Soldatis (mild--low strength) and you can get a pack of five of them for about 6 Euro. I liked the Originale as well, but the Antico and Extra Vecchio were much too strong for my tastes. Another cool thing about Toscanos is that they are meant to be shared, so it is customary to cut the cigar in half and share with a friend. They also don't need to be placed in a humidor since they are quite dry already. Finally, you can get smaller "Tocanellos' in a variety of flavors including anise, coffee, vanilla, grappa, and chocolate. At less than 3 Euro for a pack of 5 I bought at box each!
You can read more about Toscanos here:
https://www.italiansmokes.com/categories/Toscano-Cigars/
And Toscanellos here:
https://www.italiansmokes.com/categories/Toscanello-Cigars/
Prices on all of these cigars are MUCH cheaper in Italy.
Two great pipe shops in Rome--Fincato and Novelli. I'll be posting photos of each shop in a separate post when I get some time to load the photos. Purchased a few pipes during my visit.
Zack is right about tobacco though--prices there are a bit more expensive. 20 Euro for SG and 33 Euro for Rattray's 100 g tins. However, I did purchase a 50g pouch of MacBaren HH Vintage Syrian for 8 Euro which I thought was more than fair. You might want to pick up a pouch of Italia or Comune pipe tobacco--kind of like smoking a Toscano in pipe, this pipe tobacco is very unique to Italy. I passed on the Forte as it was said to be very strong, and based on my experience with the Toscano Antico I knew what my limits were.