In NYC after our first flight with baby
Our first trip was to DC, for Chris's work. Emilia was almost two months old. We drove and scheduled our departure to occur around her bedtime. She slept through the entire car ride! We even stopped to eat a late dinner and she managed to stay asleep for the entire rest stop. I over packed because 1. I'm a first time mom 2. we had a car which meant no checked luggage fees/limitations and 3. I am a first time mom!! I was a nervous Nellie so I brought everything but the kitchen sink. My electric pump. My manual pump. Emilia's bassinet. Her stroller and carriers. Her white noise machine. Books. Toys. A Boppy pillow. I could go on. It helped ease my worries to know that we would have all the comforts of home with us. We didn't use half the stuff I packed.
Our second trip was to NYC and we were flying. Emilia was just over four months old. Out of nervousness, and to avoid paying for checked bags, I upgraded our tickets to first class. It sounds indulgent but it really wasn't. The upgrade that was offered when I did our online check in was only $10 more than checking a bag. And without her stroller (since we planned to wear her everywhere) it seemed like we'd need our hands for baby wrangling more so than luggage maneuvering. I was glad we did it because not only did we get to check bags (included with first class tickets), but we got to board early. We did get a few sideways looks having a baby in first class, but I valued the extra space. And she didn't make a peep during the flight, save for the few seconds I tried to force the "nurse during take off" rule so many seasoned mama travelers suggested to me. She just wanted to look around and I was still covering up/she was still willing to nurse under a cover. I relaxed and let her take the lead during landing as well as our return flight's take off/landing. The white noise of an airplane is akin to baby Unisom.*
Our third trip was to Cleveland and we drove. It was a nice short drive and an otherwise uneventful experience. She slept there and back. I probably overpacked a tiny bit because I had a car I could fill but felt way more relaxed than when flying or when driving to DC.
Our most recent trip was back to NYC again to meet our friends' new baby over the 4th of July. We decided to drive because our flight home on the last trip was delayed for so long at LGA that it would have been faster to drive. And we saved some money by doing so. It was super easy though Emilia was old enough that she was no longer a guaranteed car sleeper. She was more wakeful on our drive home than on the way there. I think this was due to the fact that she hadn't gotten to nurse much prior to our departure and the timing corresponded with when she typically goes to sleep (so she tanks up on milk prior). I didn't over pack. And she did sleep for a good portion of the drive. Because the drive was longer than any others it makes sense that she was up (and sometimes upset) during it.
Overall, my main lessons (more so for myself than for anyone else, since every baby and every family are different) are to be flexible. Realize that cities have things you can purchase once you arrive so don't feel like you need to bring everything. A lot of the stuff you think you need, you won't. Don't be a slave to the schedule (if you are following any schedule). Our "schedule" has always been pretty baby-centered so she lets me know when she needs to nap, etc. When things are different and there are new people and stimulation everywhere, she will likely skip a nap or fight sleep if you try to time out trips back to the hotel for napping. I learned that this is ok. I came to accept that regardless of whether she napped, our trips back to the hotels were useful opportunities to relax and regroup. Sometimes she'd nap. Sometime she wouldn't.
The most useful consumer goods for us have been the Ergo, our stocked diaper bag (more on diaper bags soon), baby wipes (is there anything they can't clean?), a few key teethers/toys, light layers (for everyone but especially for Emilia), and a bottle of pumped milk. The last one is probably the most important. If we're driving and she's upset but we can't easily or safely pull over, a bottle allows me to hop in the back seat and feed her without the dangers of the "boob dangle."
My most harried moments all entailed taking her to restaurants when I knew she was overtired or when she let me know she was overheated. Her only public travel meltdowns have corresponded neatly with our reservations-required, linen napkin, fine dining plans. We try to make one plan like this per trip, so as to still get to do what we normally do during travels, but in a limited manner. We have typically booked lunches or early dinners to accommodate everyone, but especially Emilia. And we go into things willing to bail, requesting that our food be packed up while one of us takes her outside, so as to not cause too much a scene if she does get upset. We've only had to follow through on that willingness once. Every other time, if there was an issue, we resolved it and carried on as usual.
As she gets older, more independent, and more communicative, I hope that we won't lose our willingness to keep traveling. I certainly haven't lost my travel bug and every new experience is that much more joyful when processed alongside this small, curious, and brave tiny person.
*I realize this won't always be the case. And eventually it will be really stressful to fly with her because she will want to be able to run around. But while she's small enough that she can't, we are enjoying the ease of short travels.