1) Buy a slim ipod touch 2) Jailbreak (unnecessary) 3) App CryptMe allows transfer of plaintext from your computer through iTunes, password unlock on the device, quick search (nice), and according to Firewall iP (Cydia program) doesn't connect to the internet (or you could just always keep wifi off).
GPG isn't pretty, and support lags with OS X releases but you can do alot with it.
I've been using this methodology for securing cloud backups for several years. Using tools like Duplicity, you can safely encrypt data on potentially untrusted devices or networks using a public key, and keep the private key safely stored somewhere on the smartcard.
The downsides to these sorts of approaches is that encrypting data is easy, key management for decrypting it is a pain.