Q: I’m giving my third-generation iPod nano, complete with my iTunes music, to a friend in Cuba who has a computer but no Internet access. Will he still be able to play and charge my iPod through his computer?
A: Although simply syncing music with an iPod does not require Internet access, your friend will need to have the iTunes application installed on his computer, which is normally only available as a download from the Internet. Therefore, along with the iPod it would probably be a good idea to send along a CD containing the latest iTunes software installation package for him so that he can install it on his computer from CD.
Leaving aside legal and copyright issues with regards to shared music, it should be noted that if you have any purchased any content from the iTunes Store included on your iPod this content cannot be played on your friends’ computer unless that computer is authorized for your iTunes Store account, which would require Internet access. Music from other sources contained on the iPod should be playable without any problems, although it is recommended that you set the iPod to “manual mode” before sending it to him by checking the Manually manage music and videos option on the “Summary” tab in iTunes.
This will prevent iTunes from trying to automatically sync the iPod when your friend first connects it to their computer and allow them to load additional content onto it from their own computer without having to erase it first.