3rd week of February is President's Week (aka February School Vacation Week) and is notoriously expensive to fly out of the Northeast.
We fly this week every year, sometimes into Orlando, sometimes into Tampa, and sometimes into Ft. Myers, depending on our plans.
This year I think I did REALLY well. Round trip, non-stop on JetBlue BOS-TPA and RSW-BOS (into Tampa, home from Ft Myers). We paid $239 per person, all in.
However....I booked these tickets as soon as they became available. I basically have a benchmark of a 'price I can live with' and if I find something that meets my needs price and schedule-wise I book it.
We flew Delta for years, as they can be booked at 331 days out, however, they seem to have eliminated most of the non-stops from BOS to Florida, and flying in February, I do all I can to avoid stops and/or connections. JetBlue has become our default carrier. They can only be booked 6-8 months out.
For me, if I can find non-stop tickets, for $300, for President's week, I book it. If I can find it for less than that, I'm THRILLED.
We also try to skip out a day or two early to save a little bit. This year we left on a 6pm flight out of Boston, on Weds the 15th, and DS only had to miss 1 1/2 days of school (Friday was a half day) before vacation
apologies for the dissertation, but this week is so tough, I like to share whatever I can to help