If you consider music to be a part of sailing (I actually don't like it underway, but do once anchored or docked), I just began using Pandora Radio. You type in whatever genre, artist, or other phrase that describes the type of music you are interested in and it just starts streaming for free. Very very cool. I have no patience for downloading iTunes or sorting CDs, etc. I also have a wide interest in music, so my preference at any particular time can be very different from another.
I already have the cable that connected our iPod to the boat's stereo system, which will work the same for the iPad. I suspect one would only want to use this when connected to wifi. I believe that streaming music can chew up a lot of cell bandwidth.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.