We're on the same cruise.

Our closest airport is Ottawa, and the best I've seen from there is around $500/person (x4) for indirect flights. We can only get direct flights to/from Orlando from Ottawa a couple of days a week, and they're not the days I want to fly on.
I'm pretty sure I can do considerably better on Jet Blue out of Syracuse. It's a 3.5 hour drive for us, but from there we can fly direct, so overall travel time doesn't change much. My concern is that Jet Blue will release their next block of flights through to mid-March, which would cover our departure date but not the return. If that happens I'll have to decide whether to book the outgoing flights immediately (bit of a risk, since it more-or-less forces us to fly back to Syracuse no matter the price - our car would be there), or wait until the return dates are available to book the round-trip. If the outbound prices are good I'll probably opt for the former and take a chance on the return; our return dates are at least somewhat flexible, but our departure date really is not.
Anyway, just wanted to say that you're not alone. Waiting around makes me nervous, especially for March Break flights. Good luck!