I swear I haven't done as much planning (or stressing) about a flight/trip as the one we will be taking next week. I've braved my first flight with the little one (solo even) and was able to bring most of his essentials in a backpack style diaper bag and everything else in a carry-on. Now he's eating solids consistently and will be heading on a two week vacation to his grandparents (where there hasn't been a baby in the house for oh 25 yrs?)... this is the first time where packing for a little one really is packing for a third person, haha.
We've taken his Rock and Play sleeper for road trips and that's worked out well. When I flew to OH for a wedding, I just had him sleeping on a blanket, on top of the covers next to me. Now though, he's a wriggly little boy who likes scooting upward while on his back as well as rolling over.. in the end, we bought a Pack and Play and had it shipped to my parents house (and leaving it there for our next visit).
Since he is an independent sitter, we've been taking him out of his car seat and putting him a high chair when we go out to eat. When we drove to UT for Thanksgiving, we brought his Bumbo along for a feeding chair. Since I wasn't planning on packing (or re-buying) that, I bought this: http://www.amazon.com/Brica-Travel-Booster-Black-Green/dp/B004L2JJ6O/ref=sr_1_1?ie=UTF8&qid=1355504588&sr=8-1&keywords=brica+booster. Looks like it can fold up so I can put it in my diaper bag (will keep you posted on if this actually folds down that small). Hopefully if it is truly that portable, we can use that a lot more when we go out to dinner. I did find this and it goes on most standard chairs: http://www.amazon.com/Trendykid-TS007-TrendyKid-Totseat-Black/dp/B004TVODAO/ref=sr_1_4?s=baby-products&ie=UTF8&qid=1355504658&sr=1-4&keywords=my+little+seat I didn't buy it after reading customer reviews. It did say that it was easier to get set up than the similar My Little Seat fabric highchairs. However, it didn't dawn on me until I read the comment but these fabric highchairs aren't high enough to get the baby to table height.. that won't work for my social butterfly cause he needs to see everything!
As far as feeding, I plan on also bringing a couple of these: http://www.amazon.com/Plum-Organics-Just-Peaches/dp/B003QZM3LA/ref=sr_1_3?s=baby-products&ie=UTF8&qid=1355504935&sr=1-3&keywords=just+peaches for quick feeding at the airport or on the plane. Best part is you can totally just squirt it into his mouth! I've also been able to prep some of his first foods so I will also be bringing mashed avocado in one of these: http://www.amazon.com/OXO-2-oz-Freezer-Storage-Containers/dp/B006YTW612/ref=sr_1_3?s=baby-products&ie=UTF8&qid=1355504885&sr=1-3&keywords=oxo+tot+baby+blocks+freezer+storage+containers. He also loves bananas (another easy prep option that doesn't need refrigeration).
Even though we use cloth diapers, we use disposables when we travel. Last time I flew, my husband helped me prep and we decided that in order to cut down on all the stuff I would be carting around, I needed to pack only the number of diapers (plus 1-2 more) to get through the flights & layover... as soon as I got to my destination, I bought more diapers for the rest of my stay and enough for the return flights and layover.. and left the rest. We are probably going to do the same thing this time around.
Since he's a great traveler, I'm not bringing any more toys than what is already in his diaper bag. He did great on his last flight (even if it wasn't nonstop) and slept most of the time. I am definitely bringing an Aden + Anais blanket for something for him to hopefully nap on (at the airport or if we're lucky enough, an open seat). I'm also probably not bringing our Ergo Sport carrier cause my husband will be another pair of helpful hands (this was a must when I was on my own, though).
As far as future flights, I found a couple of things to keep in mind. This is the next car seat we will be getting soon for him. (http://carseatblog.com/17513/cosco-apt-review-does-it-compete-with-the-scenera/) It is FAA approved so we can use it on the airplane, but most importantly allows us to keep him rear facing up to 40 lbs. He won't need to be in a car seat on the plane until he's two so chances are we'll be gate checking this car seat for a while but this product (http://www.amazon.com/dp/B0074JKQ0Y/?ref=cm_sw_r_pi_dp_4JZYqb176SE6X) will also be good to keep in mind. :)
Hopefully this cuts down on all the stuff we'll be bringing along; inevitably we'll be coming home with more stuff than what we left with haha.
What are some of your tips for holiday traveling with a little one?