I have iPod playlists for various stages (and moods) of a trip:
Waking Up Easing into the day with a cup of tea/coffee in the cockpit. Classical and instrumental music
Underway Upbeat, excited that the motor is off. Reggae (there's more out there than just Marley, good as he is

), some classical, classic rock, sea shanties, trop rock, etc.
At Anchor Relaxing with beer/wine and good food. Blues, traditional jazz (none of that so-called "smooth" jazz nonsense), standards, acoustic singer-songwriter tunes
However, we have yet to listen to any of the music that I spend time collecting actually on the boat. We like to hear the burble underway, or the near-silence at anchor. We turned on the radio only once at anchor and that was to listen to a Phillies game.
Mostly I play my playlists while puttering around the house.
Maybe I should change the playlist titles to:
Cleaning (or Moving Stuff Around) the Garage
Cleaning (or Moving Stuff Around) the House
Gardening