The most reliable music schedule is at http://seestjohn.com/arts_music.html

Winter break there will be a lot going on. Hopefully the north swell won't come up. Caneel Bay mooring and a dinghy ride to Cruz Bay is going to give you the most access to "beach bars, live local music, local fare, meet local people" and access to Salomon and Honeymoon Bays for beach time. The ferries make for a rolly mooring.

Leinster Bay is the most remote spot with great snorkeling and no cell phone coverage from USVI or BVI. Francis Bay is pretty protected and adjacent Maho Bay makes for a killer stop. Sadly, Maho Bay Campground is closed, so no meals or music at the pavilion. Cinnamon Bay has a small restaurant and showers and Trunk Bay has a snack bar and showers..

Cheers, RickG