I know you're into music so you could tour a bunch of sites related to music history and go to see some live shows along the way at interesting venues. Here are some possibilities:
- SXSW (now!), Emo's and various other sites in Austin
- Graceland and the Sun Studio in Memphis
- Grand Ole Opry, RCA studio B and various other sites in Nashville
- The Experience Music Project in Seattle
- Rock and Roll HOF in Cleveland
- The Apollo, CBGB Festival (the original venue is closed), 53rd and 3rd (where Dee Dee Ramone hustled for drugs), the Dakota (where Lennon lived and died) and the Chelsea Hotel (where Sid killed Nancy) in NYC
- The Stone Pony in Asbury Park
- Theresa’s Stockbridge Café (formerly Alice's Restaurant) in Stockbridge, MA
- Preservation Hall and other sites in New Orleans
- Amoeba Records, Dane's House, Whiskey-a-Go-Go and various other sites in LA
- Hitsville USA museum in Detroit
These are a few that I pulled from either my own head or
this list. I'm sure there are quite a few other great music related museums and venues you could find depending on the part of the country you wanted to be in and your music interests.