We did a trip to NY/Toronto when our daughter was 4 months and then my wife took her to ON by herself when she was 9 months (all before COVID of course, we’ve been stuck at home since then). It definitely was a lot of work. Our daughter didn’t sleep much during both trips, which definitely makes it even harder.
I think the big lessons for us was just how much crap we needed to bring with us (car seat, stroller, travel crib) and how to make plans that could be flexible or cancelled if necessary. We went for a wedding and everything went well until the supper when our daughter ran out of steam and there was not an easily accessible quiet place we could take her to settle her down, so had to call it quits and grab a pizza on the way back to the hotel. I remember it felt like we had “two hour windows” during the day between naps and feeds, which doesn’t allow for a ton of sight seeing. The other thing was trying to find a hotel room big enough for all the stuff, which was a bit tricky in NY.
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