I'm in the same boat - except we leave with our squirmy 13 month old in 15 days!!!
She has flown down there 2x before, but I'm sure this will be the toughest. Each time she had her own seat w/ carseat, but I can't even get her to sit happily in that in the car - but it was great to slip her in there once she fell asleep.
The good news is that our flight to MCO leaves at 8:30PM, I'm sure she'll fall asleep at some point! I plan on having **SNACKS** (toys do nothing if she isn't in the mood) and getting some stickers (which she just gets a kick out of ). Of course, my "secret weapon" is that she is still breastfed- which will calm her down pretty much instantly if need be- and it also helps relieve the pressure during take-off/landing. Knock on wood, she has yet to cry on the plane. (I am probably jinxing myself now!!)
As far as the airport/parks/etc. Airport, she will just need to accept being in the stroller while we trek to the gate (maybe I'll offer up some goldfish or grapes as a bribe!) and in the parks, we will take the stroller, but she will probably want to walk most of the time so we ordered a baby harness. It only has about 2ft of slack, no farther than if we were holding hands, but she doesn't need to walk with her hand up over her head and it is safer. We'll also carry her a good bit I'm sure (she's not quite 20lbs yet, so its still manageable). There really is no baby carrier that she would accept being in for any lenght of time.
In all honesty, I don't think benadryl is a horrible idea, especially if you are worried about ear pain, as it helps reduce sinus pressure. Before our last trip, we tested it out (it can make some children hyper)- just in case she had conjestion before we left or developed some while we were down there. If we had a rough flight down, I would not have hesitated to use it on the way home. I don't remember the dosage - but the doctor told us hoe much to give.
Have a great trip!!!