There is plenty of live music on the island. For some restaurants and bars, it's an everyday thing.
Aqua Bistro and Island Blues in Coral Bay reliably offer everything from blues to rock. La Tapa in Cruz Bay regularly features soft latin jazz-influenced sounds. There's the Wednesday Night Jam at Sun Dog Cafe, where it's always Open Mike time. Sunday afternoons at the Beach Bar are always lyrical.
Inner Visions - world famous reggae band – could pop up at Fred's or the Beach Bar. Check out one of their most recent CDs on Amazon: Finally Captured Live
Marty Beech, often at Caneel Bay's Turtle Bay restaurant, croons in the Sinatra manner. Preview Marty's CD on Amazon: Summer Wind – a Tribute to Frank Sinatra
Mark Wallace has been on the island for more than 20 years, comfortable as a solo with a guitar or as the leader of a kick*ss uptempo group playing a wedding reception. Mark self-produyced his CD which is available on Amazon.com: Cornerstone
Victor Provost grew up on the island, learned the steel drums/pans, left to study and perform, and became a pan star. While he lives in the states now, occasionally he returns home and plays. His latest CD is on Amazon: Her Favorite Shade of Yellow
If you can hear any of these pros while you're visiting, don't miss the chance. And lend an ear wherever you hear live music because there are dozens of other talented and entertaining singers and players who want you to have many happy musical memories.