can be done with an (OpenSource) 3rd party tool called iTunes Agent

What does it do?

iTunes Agent is a tiny application which rests in your system tray, constantly looking for devices being connected to your system. If a device it recognizes is connected it enables you to manage it via a playlist in iTunes. You may even associate your player with a Smart Playlist, such as “Party Shuffle”, and always have a new collection of tracks on your player!
When you are done modifying the list of tracks for your player you can synchronize it with two small mouse-clicks!

What devices are supported?

Most mass storage devices should be supported. The only criteria for iTunes Agent to be able to synchronize your device is that it is mapped to a drive letter under “My Computer” in Windows.