I took my 17 yr old DD to HHI last year and evenings were a challenge for us! The Island activities pretty much shut down when the sun goes down! We did the movie theater one night (hard to find due to signage laws), shopped the little mall, walked around the marina area which had alot going on in the evenings with vendors and musicians and planned some dinners down by Harbortown/Sea Pines which kept their shops upon late. Alot of restaurants had outdoor dining with live music, like the Boathouse. We stayed after dinner and listened to their band which was really enjoyable. The resort had two teen nites out while we were there but she opted not to go.