We have been traveling around this time the past few years. Have a back up plan on top of a back up plan!
Last year we were scheduled the day after Christmas and despite not being ON a Southwest flight that was the cause of the nightmare, we awoke at 3AM to go to the airport to find our Delta flight was cancelled-not delayed, cancelled with no outgoing options for 3 days. We lost our water taxi reservation (which note, you will not be refunded if you don't show that day) and had to drive to a different city just to fly out and get there two days late as opposed to three.
Carry lots of trip insurance and try to have multiple plans.
This year I pushed us to the 28th but I am still planning on having multiple plans of attack.