What are the suggestions for a good dinner and hopefully some good music, not necessarily in the same establishment, on Weds afternoon/evening on 5/29?
Definitely Quito's for food. If anyone in your group likes tuna, the Wicked Tuna is my favorite dinner on Tortola! Generally, you will find Quito playing solo on Wednesdays. I think Kim caught a night that Quito was not on Tortola but you should find him there.
If Quito's doesn't work out for any reason, I also recommend trying Banana's, although it's not on the beach. It's directly across the street from the parking by Myett's.
Cheers,
Jason