I've been using my iPod for a while now on those long paddles by myself..I love my music.
I bought one of these a while ago and when I get my Naish Glide I will put deck plugs in it so I can mount it on the deck in front of me..
It sounds great..and comes with straps so you can wear it like a back pack..The guys down at St Kilda pier will freak as I paddle past with my music blairing.

I have been using the new iPod shuffle and a couple of weeks ago bought some nice new earphones that clip over your ear..They work well and are cumfee but you need the volume up more to get a good sound.
My iPod shuffle and headphones are not waterproof..but you rarely fall in cruising on flat water..The iPod shuffle is only about $45 now and there are many other cheaper mp3 players out there.
DJ