Interesting that you want to hear while taking a nap. I was hearing until 4, and no matter what, I cannot fall asleep if I am hearing something.
When I go swimming, the last thing I would want to do is bring my CI in the water for several reasons...1) Chlorine is corrosive to just about everything, 2) If it comes off my ear, will I be able to find it in a lake or a 10 foot deep public pool? and 3) Electronics & water do not mix, period. I don't care if everyone advertises their CI's as 'water resistant for 30 minutes in 2 feet of water', I ain't putting mine in water, especially when I will have to pay for any repairs caused by misuse.