[jeffgrant]

And I'd recommend doing this for transferring your iTunes files:

-- copy the iTunes song files from your Windows machine to the external drive

-- if you have any playlists you like, you can export them as XML files. These playlists aren't the songs themselves, just the list of the song names, etc.

-- connect the drive to your Mac

-- don't copy the files to your Mac like you normally would think to, but open iTunes and import them into your Mac's iTunes. iTunes has an "add to library" menu item (under file) that you can point to the top level folder on the external drive that has all of your songs in it. iTunes will then copy the songs from the external drive into your iTunes, and process them and add them to the appropriate databases, etc. Normally copying the files won't actually import them into iTunes, but this will.

360GB will take a fair bit of time just to transfer to the drive, never mind importing them back into iTunes, but you'll only have 1 action to do compared to using a thumb drive or DVD's, and it'll be way, way faster.