We have Sailing gypsies through here all the time. Last crew, all musicians, surfers too, picked up some wreck in Africa and made her seaworthy between them. Now they sail around the world, stopping only at surf or tourist destinations, if the two combine in one location they stay for a bit. They play the local haunts wherever able to pick up gigs, helps that they are super versatile in terms of range, they do everything from weddings and bars to chamber music.
Got them super baked one day and was treated to an impromptu concert/jam session I will never forget. Sunset, stoned, swaying to and fro as these people did their thing... it was dreamy actually.
Pretty cool lot, threw it all away and live doing what they love most... sailing, surfing and entertaining.