When we book the flights, we always talk ourselves into booking an early, early flight at the start of the vacation. But when travel day arrives, we routinely complain to ourselves about having to wake up so early and vow that will book a later flight next trip but we never do.
On balance, getting on the first flight of the day has worked really well for us as we always enjoy having at least the full afternoon and evening of our first day of vacation to enjoy at WDW.
However, on one trip, the early departure was a life saver. It was March break and we were booked on a 7-day
DCL cruise. We were flying down to Orlando early to spend a fews days at WDW beforehand and were booked on a 6:30 am AC flight from Pearson. The night before I had photocopied the picture pages of everyone's passport (in case somebody lost their passport on the trip) and forgot to retrieve my youngest daughter's passport from the photocopier glass after copying.
We arrived at the airport just over 90 minutes before the flight and I only realized at the AC check-in counter that I did not have my daughter's passport, though I did have all the photocopies. Rebooking our family of 5 on a later flight that day was basically a non-starter because the AC flights to MCO were booked solid that day and for the next couple of days; they couldn't even assure us of getting two seats for later that day. Even if we were able to get through U.S. customs at Pearson on the basis of the photocopied passport page, I was concerned that DCL would deny my daughter boarding on the cruise without the passport. I was basically panicking like crazy inside at this point, as was now less than 75 minutes until the flight departure.
I decided to check-in us all in for the flight and send my wife and 3 kids to the U.S. customs line to try to get through with the photocopied passport and catch the flight. Meanwhile, I would try to race home to get the passport and, if I didn't make it back in time, I would go on standby for the next available seat...but who knows when. I raced down to the taxi cab / limo stand at the arrivals level but, of course, there was nobody there since no flights arrived that early. I then ran to the long-term parking lot at Terminal I (thank god we parked there) grabbed our van and drove myself home, usually a 20 minute drive each way when traffic is light. I would be embarassed to say how fast I was driving and, as there were tracts of snow on the 401, the driving conditions were not the best. When I got home, my daughter's passport was exactly where I thought (or hoped) it would be and, miraculously, I made it back to the airport, parked the van and returned to the AC check-in counter with about 15 minutes to spare. The AC agent called ahead to the gate to advise that I had arrived and, as there were no line-ups at U.S. customs yet, I was able to quickly clear customs, sprint down to the gate and get on the plane just as they were getting ready to shut the door. Needless to say, I was only able to get home and back and through the airport in time because of how early the flight was.
I have no idea what we would have done if I did not make it back to the airport on time, as my wife and I hadn't the presence of mind to work out any of the logistics with that scenario.