Bubblehead, when I have young ladies in the boat, which is much of the time, I do my best to accommodate their wishes and demands. Most of the time, I'm not playing music, just letting them sail the boat, while I prepare their food and mix the Green Coconut Margarettas. Yes, I'm a galley slave, and damned proud of it!
One of the best aspects of sailing Chesapeake Bay is weekday sailing. I usually try to schedule at least one day off in the middle of the week for sailing, mainly because weekend weather and boating traffic usually suck. It rarely rains on Wednesdays or Thursdays, and the winds are usually better, west to northwest, or maybe east, all of which allow me to put the sails up as soon as I get south of the Amtrac Bridge at Havre de Grace. Then I just give the wheel to one of the ladies, go below and break out the chips and snacks, mix a couple cold drinks, and enjoy a beautiful, quiet day on the bay.
I guess because I play music for living nearly every day of the week, and lots of nights, the solitude of sailing and not hearing the music anyplace but in my head is kinda a respite from my day job. No different that anyone else that enjoys a day away from their regular routine.