A few places I know well
Paris, France
I’ve been twice. The second time was multigenerational — three generations in one city, everyone wanting something different out of the day. That’s the version I’m best at. The museums are worth it, but not three in one day, and not for everyone in the group. I book the hotel for where it puts you at eight in the morning, and for whether the rooms actually work for who’s sharing them.
Vietnam
Six days in Hoi An and a few in Ho Chi Minh City, and it’s the trip I recommend most to families who think it sounds too hard. It isn’t. The food is the best I’ve eaten anywhere, the tailors in the old town will make you something in a day, and a resort on that coast costs a fraction of the same standard in Europe.
Mexico’s Caribbean Coast
The one I book most, because it’s under three hours from Houston and barely a time change. We spent Christmas on the Riviera Maya and Isla Mujeres with another family — half at a resort, half in a private house. Two families in one hotel means two sets of rooms and separate bills. A house means one kitchen, one table, and somewhere for the kids to be loud at seven in the morning.