re: People with experience traveling with multiple children ~2 years old

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Also keep in mind you will need to haul around the baby gear, stroller and maybe a car seat.

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This is what broke us. We would go "camping" with our kids, and it looked like a freaking Everest expedition. Keep in mind, I've spent two weeks on trail with a backpack and food drops, so filling up the entirety of the bed of my Tundra for two nights of car "camping" felt insane. We weathered those years with some camping trips and yearly trips to the beach. Got in a trip to Idaho and some others as well.

My initial advice was to stick to the beach because it's easy. Even though we mainly did the beach (and those were most enjoyable) the fact that we attempted some of the other trips now makes us appreciate the ease of travel with 11 and 8 year olds. Just did 2 weeks in some remote parts of Costa Rica with them this summe, and it was awesome. Did Spring Break in Santa Fe, and it's amazing having your 8 year old wake you up before dawn ready to go mountain biking on some trails in the morning.

So while I do think some trips are more fun with that age than others,'I do subscribe to the idea of getting them traveling and used to the "chaos" of being off routine, having things go wrong and most importantly just enjoying the moment can be beneficial for later travel experiences. My kids are kind of game for anything and will sit down to a two hour dinner with no screens without complaint. We built that through travel.

On the other hand, we know people (rich) who would go to Italy for a month with their very young kids. They'd just plop their kids down with iPads at dinner, and not give a dam about looking like ugly Americans. We don't allow that shite.