It's not really hard. Put the baby in the stroller and the carseat on someone's back in a carseat satchel. Keep your carryons to the absolute minimum, except that you should carry food/drink/clothing for baby for 24 hours, and a spare shirt for each parent. More than one rolling carryon will be a nuisance if you are pushing a stroller and carrying a carseat; stick with a backpack if you can. No purse for Mom, either; put the essentials in the diaper bag.
Remove all extra parts from the stroller before leaving home, and put them in your checked baggage, including the hood if it comes off without tools. Do not use the stroller basket while in transit, you must fold the stroller for the security x-ray, and to gate-check it. (Fold and secure it yourself, DO NOT expect the airline to do it properly. I recommend a bungy for extra security.)
OK, more re: security: if your child doesn't walk yet, don't bother putting shoes on at all when travelling, just go w/ socks. If he does walk, bring a set of walking reins to keep him from escaping while you get through security. Also, don't dress baby in overalls that have metal fasteners; they can set off the alarm. Make sure your own shoes (Dad's too) are slip-ons. Take off all outer jackets, belts, etc. and put them in the carryon or carseat satchel before you approach security -- with the kid to wrangle it's best if you don't have to participate in the undressing sideshow. (Oh, and empty your pockets, too, the only thing in them should be your id and boarding passes.)
Get a laptop sleeve for dad's laptop, and carry it inside the daypack. Any cords, etc. can go in the checked bag. I agree that he won't get to watch anything on the plane except maybe the Wiggles, but the reason that I'm not telling you to skip it is that on your first trip w/ baby you're likely to take a gazillion photos, and he'll want it for downloading them.
It *is* still possible to pack light with a baby, but you have to redefine your definition of light. The most important thing is to let go of the idea that light = carryon only, because the carseat and the stroller make that more trouble rather than less. Check a bag, but make it one large bag for everyone. (Of course, not TOO large, you don't want to go over the weight and size limits.) I find that my definition of "light" now revolves around how many pieces we take rather than their size; if we do one carryon, the stroller and carseat, and one checked pullman, we're able to navigate any subway in the world, and that's light enough for us.
Hubby & I will be taking our 4 daughters.....our newborn who will almost 4 months, our just turned 3 year old, our 4 1/2 year old and our 12 year old (who happens to be legally blind)....so that's 3 carseats, I decided to bring the tandem double stroller, baby in a maya wrap sling and our visually impaired 12 year old...........and I have no worries, so you will be fine. I promise you, you will actually be wonderful and no one will be staring at you with 1 child going to Orlando as there is always some crazy family like mine on most flights there that help divert everyone's attention!!!
Maybe your baby is different & either will fall asleep or watch the movie with him, but that NEVER happened to me.
