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We've done 2 plane trips (one at 5 months and then just a few weeks ago) and several 5 hour road trips. For road trips I try and usually hold off her nap until we are ready to leave. Or, plan that she'll take a nap about an hour into the trip. I pack lots of snacks and a portable dvd player or laptop. And, when awake I'd try and stop about 30 to an hour into her awake time and let her run around and stretch her legs a bit.
When flying - at 5 months I just bf'd her when she started to fuss (even if more often then she usually ate) to keep her quite and calm. More recently I just gave her her pacifier or a snack when taking off and landing or try and plan for her nap to finish around the time we are landing so she'll be asleep and wouldn't notice her ears bothering her as much. She had toys and lots to drink and a variety of snacks to keep her busy. I packed the dvd player but she never used it on the flight. About 2 different times I'd let her get out and walk the aisle and let her stretch her legs before sitting back down.
No I haven't traveled much with Carson, I have flown several times with my older 3 boys - all of them vs me on a plane was... well, not as bad as I thought lol. We are thinking of driving to DC this summer on a little vacation/road trip and I'm a bit worried because he doesn't really care much for being in the car but he'll be older so he might be better by summer in the car. My biggest issue is that every trip we take at least one, if not two of my boys get car sick and that's never fun!
Caeden flew when he was 10 months and again at 16 months--both times went well. Though the second time I was thinking next time he will have to have his own seat. It was a bit more difficult as he wanted to run around more the second time around. I put him in my Beco carrier though and that helped a lot. I recommend keeping them strapped to you--it gives them less options to get into mischief.