Jazz Corner is the place to go on Hilton Head for the special night. It's tucked back in the corner :) and is this local's favorite. The musical line-up is varied, from blues and jazz, to southern shag played by local legends as well as national names. I believe there is a schedule on their website but we never check and have never been disappointed with whomever is playing.
Make a reservation and enjoy your table for the evening. The extensive menu will provide ample choices (my faves are shrimp Dejong and the Jumbo sea scallops) and the service is impeccable despite how loud and crowded it gets. Enjoy!
Pros: great food, great music, intimate setting