All you have to do is download this great app called Pod to Mac.  It is so easy to use I could probably just stop now, but I will give some quick instructions.

Literally all you have to do is open the application and plug in your iPod or iPhone and it will automatically display all the data on your device so that you can search through and decide what media you would like to transfer to your computer.  The great thing is that it not only transfers music, but can also transfer video and pictures (coming soon) from your iPod or iPhone to your computer.  Just select the files you want to transfer and click ‘Transfer Files”.  It is really that easy.  After you transfer your files, go into your iTunes Music folder and you will see all your files automatically organized nicely and ready to be played in iTunes!

Another great thing is that you don’t have to put your device in ‘Manually manage music and videos’ so you don’t have to worry about messing with any settings at all (this is iPhone and iTouch only I believe, I think for older iPods you do have to put it in ‘manual’ mode).  This allows you to continue to automatically sync your device when you plug it in which I really like.

The only thing you do have to do is make sure that in iTunes, under Preferences > Advanced, both ‘Keepy iTunes music folder organized” and “Copy files to iTunes folder” are checked.  I believe those are checked by default so you should be good to go.

No other program I have tried works as well as Pod to Mac.  I definitely recommend it if you are looking for a quick and easy solution to transferring music from your iPhone or iPod to your computer.