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I would recommend a family cruise. So far nothing has been easier traveling with kids than a cruise. Cruise ships have so much for kids to do, and also for adults. It’s a good balance. And since you’re on a boat, there are no logistics since you are on the boat.
I agree with the all-inclusive approach because there are less logistics. This will make for a less stressful, more enjoyable vacation. With that being said, it depends on the temperament of the child. We've had successful vacations in Gatlinburg and at Disney with our daughter at that age. I have four children; she is exceptional ;)
OBX
PCB 😎
Marco Island
We took the family to Atlantis when our kid was about that age. Our kid was a fish at that age, so the pools, water slides,, and beach kept him busy which resulted in long naps and sleeping through the night!
We stayed in the high end buildings so we could have plenty of space and have a separate bedroom for my wife and I.
Just drive to 30a or pcb. Get a house or condo so they can have their own room so you can put them to bed early and stay up.