Ok I may be wrong, but wasn't it mentioned that the Queequeg was in Lake Anwhistle at some point. Perhaps Josephine organised to escape from Curdled Cave in the Queequeg, and was simply biding time until then? Perhaps with Hurricane Ivan predicted it wasn't feasible to leave town by another means, or perhaps she noticed Olaf had his henchmen set up at the border, or perhaps her fears kept her in check.
I know I'm reaching, but in theory it works, right?
That's a reasonable connection to make, yes; the Queequeg did patrol Lake Lachrymose for years, with Widdershins knowing Josephine personally. It doesn't do much for the circumstances of Josephine's recognition of Olaf, though, those being that he flirted with her and then called her on the telephone and just told her that he was Count Olaf.