Alright it's working again. (Restarted the computer fully which usually fixes these types of glitches ended up working)
This sounds a lot like a bug I was having a while ago. I just have to ask, do you also play Wizard101, and if you do, when Pirate101 does not load, if you try Wizard101 does it say that you're not connected to the internet?
If that's the case, the fix might be even simpler than restarting your computer, simply go into internet explorer (or what ever other internet browser you use) and make sure that your browser is not set to "Work Offline" mode.