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@Adira: We traveled to Italy (Venice) when LO was 5 months old and London and Ireland when he was 10 months old, so again not a toddler but happy to answer any questions about logistics! It worked out amazingly well both times, and LO had no problems adjusting to the new time zone. We tried to make sure his first nap was in the hotel, and his second was pretty much always on the go (either in a stroller or carrier). Venice would have been impossible with a stroller (we used the carrier), but I think Rome would probably be fine. Italians were incredibly friendly, and loved cooing over the baby.

You should absolutely do it! I was nervous to take my toddler on a vacation, and it turned out to be one of the funnest family experiences we've ever had. I'm so sad that she won't remember it when she gets older.