We thought that, too. We were planning to leave from Providence, but our flight was cancelled. So was every flight from Boston, Manchester, and Hartford. And every flight from New York and Newark, too. There wasn't a single flight in the area that could get us to Orlando early enough to board the ship the next day. We considered taking the train and that night and then flying the rest of the way to Orlando the next morning and that almost worked. If we had found out about the cancellation an hour earlier, then we could have taken the train from Providence to Baltimore, spent the night near BWI, then got on a flight to Orlando in the morning. But, unfortunately, we didn't find out an hour earlier. The other option was to take the train to New York, catch another train out to JFK, find a hotel near JFK, then catch a really, really early flight to Orlando in the morning. But there were too many moving parts with that plan and we wouldn't have had much time to sleep at all, which would have made for a rather bad first day on the ship.
Anyway, it's all good. We just swapped our 7-night cruise for a 4-night and a 3-night. I think I'd rather have two days at Castaway, anyway, and we got to do the back-to-back thing for the first time. The only downside was eating the same menus twice.
But from now on, I'll fly 2 days ahead in the winter!