We all have insecurities. It is what we do about them (i.e., not panic/ stress and deal with them rationally, etc.) that matters. I would bring up the trip for sure. He invited you once, maybe he doesn't think he needs to invite you again and that you don't seem that interested in going so he doesn't want to push you to come along to watch his band. He could be feeling insecure too right now.
I think you could easily ask if the trip was still on, what his plans were with respect to the trip so you can make plans too and/or that you are really exicted to see him play in Florida. Any one of those options would lead to a better understanding if he still wants you to go (I'm sure he does).