hi, I think I can help a little...we just returned...where r u staying, beach or cliffs, if u dont want to give out hotel, maybe just the area...ok slow season so the choices for live entertainment is limited...tues is alfreds on the beach, wed is dj at bourbon beach, live music at roots bamboo, but one of the two weds nights it didnt happen, thurs is west end gang live at bourbon beach, fri is alfreds again and saturday is cant miss seastar party....keep in mind alfreds and roots are gonna b later getting started as most of the live shows are....west end gang and seastar shows actually get started earlier and are the ones my wife like, I am 49, she a little younger, did our 23rd anniversary last week...seastar has nfl ticket, but not on water, bourbon beach has a big screen they set up for football, Margaritaville for more commercialzed, and expensive,setting, but most places will turn their set to a game if requested...
the pub crawl listed above the the best way to meet people and see different places on the cliffs...we did 8 bars in about 5-6 hours....those would b the 3 cant misses in my opinion to get the expierence u asked about in your post...I have the same requirements as u on most of the above so I hope this helps...
bourbon beach has good jerk chicken, but everyone has their favorites on food,
