Have been to Italy a few times including Rome and Florence. Found there are very few bars to meet guys and certainly not the cruisy type of bars. And in Italy men are very much in the closet is my experience (maybe I'm wrong but that's my experience). However I had no problem finding raw dick using PlanetRomeo.com (free). Just change your location to where you are staying and you can see how far away they are. You can state in your profile wether you like it raw, safe or leave it open for discussion. Create a travel plan so they can see you are visiting (do that upfront, not when you're already there). State you're an American looking for raw loads and they will be all over you. Maybe because you're foreign and they will likely not bump into you socially. Do the same when you're in Florence. I had plenty of anon raw fucks, especially in Rome.
And try the bathhouse in Rome. More mature crowd as in the others: http://www.saunamediterraneo.it/mobile/inglese/index.html Guys were all over me once they find out I didn't speak Italian. Went back several times and always good for a few loads. You need an Arcigay card to access but you can buy that there at the reception desk. Use the doorbell (first time I went there I thought it was closed).
You may think of renting an apartment rather than a hotel or B&B if you want to receive or take them home. Although some B&B's don't have someone at reception after hours. And I once stayed at a B&B next to the Vatican with a horny host who is into older guys;-) There are listings for gay B&B's and hotels, not many 100% gay but google them.