One of my Christmas presents was an mp3 player for use when I'm in the pool.
Merlin Swim MP3
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Transfering music is simple but it has to be in mp3 format. Most of my music is in m4a format but that wasn't a problem as I have Real Converter which did the job for me. Some of my music is in m4p format and I don't really understand why Real Converter can't handle that. Something like Converter Lite might be able to do it.
The controls on the player are simple to use and there is a selection of ear bud sizes (waterproof and normal).
Looking forward to using them when I'm next in the pool.