Ubuntu – Complete iPhone backup without iTunes

iTunes on Wine is the closest thing to "native" you'll get but it's not supported very well and you won't get device syncing.

iTunes through VirtualBox is probably going to give you the highest quality experience.. You'll probably be able to use devices (read: iPods, iPhones, iRacks, etc) as you would with a real Windows install. It's just heavy.

I do wonder why you want to run iTunes. If it's just for purchasing, playing and syncing audio files, there are alternatives (Rhythmbox, Banshee, Amarok, MPD+Frontends, etc) that are arguably better and are truly native applications. They just take a little getting used to.

I hope my answer won't be too generic, as I have little to no experience with iPods etc, but perhaps you might still find this useful.

The problem might be that Wine "sees" the iPod through the Linux drivers, which makes it very different from connecting your iPod through Windows or Mac. iTunes expects to see a USB device with a certain driver, and because Linux intervenes here, it will see a different one that it cannot recognise.

If this is true (and if anyone reads this, please correct me if you DID get your iPod to work through Wine), I'm afraid it will be very hard to get your iPod to work through Wine.

There are plenty of Linux native alternatives available though. For example, Rhythmbox claims to support iPods through its plugins.

If you want to read more on iTunes user experiences with Wine, try WineHQ.

Update: izx has another good idea if you want to run iTunes on your Linux machine and be able to synchronise your iPod: set up a virtual machine (e.g. through VirtualBox). If you then enable USB support you should be able to synchronise your stuff. Again, I cannot confirm this from my own experience, but it seems that izx is usually right :)