The day of departure, especially when you have a late afternoon flight, so you have "sort of" a day and are wondering what to do. Reality is just staring you right in the face. It's awful.
Definitely the last day. I was dreading the last day before the vacation even started. It went out of my mind during most of the vacation, but you just know its coming. You plan and get excited all year for this vacation and its such a bummer when its over.
Watching the forecast for the day you're supposed to fly to Orlando and hearing that a big snowstorm is supposed to start 6 hours before your flight time.
I've had ALL of those things happen, and trust me, the absolute WORST is getting sick on the vacation, b/c I don't wanna go on any rides, b/c I don't wanna puke on anyone, I can't leave the park b/c I don't wanna get so far from a bathroom (tram ride to the car, car out of the lot n 2 the hotel, park in the lot and go find your room)........
Losing your beloved Grandma, who basically raised you as a child, 3 days before you are scheduled to fly to WDW and not being able to change your airline tickets so you can attend her services as they were all over booked for the christmas season. It really took a lot of Disney Magic to make our trip enjoyable. I had to hold on to Grandma would have wanted us to go and enjoy - life is for living.