Here is an example from World Nomads which I found by Googling "italian language free course ipod". You might consider a language course - there are various options available from tutor-based courses at your nearest metrotropolis to CD or web-based information. We will issue some recommendations.
Since most people have a limit on their time, we need to maximize our time during our holiday. We are aware that for some of you, that might mean taking an organized tour and let someone else do the driving. A coach tour is a great way to start but you're missing out on a large part of Italy, namely contact with the people. In these few pages we will suggest how to organize your own tour, even adapting your itinerary as you proceed.
One consideration is language - the standard of spoken English varies enormously through Italy. In hidden Italy which, by its nature, is off the beaten track, you don't find so many Italians able to understand you shouting at them in English, no matter how sympathetic they might be. It is a very good idea to have some very basic Italian - when you leave your hotel you can meet ordinary people and find your way around. Italians will try their utmost to make themselves understood, resorting to hand gestures if all else fails. More of the younger generation have good spoken English in hidden Italy - but the older generation are, in many respects, much more interesting if you can understand them. They will speak slowly if you ask them politely. If you are a beginner to the Italian language, I recommend an inexpensive tourist phrasebook. At least you can learn the essentials such as "yes", "no thanks", "would you repeat that slowly, please" and "where is the toilet?"! Another alternative is to download the increasing number of free (or paid) internet language courses; many of these play through your iPod (I don't have one but can play iTunes music through my computer and laptop).