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[quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous]Places we have been that went poorly: Portland/PacNW, Colorado, NYC. [/quote]

What are you trying to do on your vacations, aka what do you consider fun? If the best vacation so far was Disney, sounds like your family might benefit more from a beach or other laidback vacation rather than a city-based one built on sightseeing and restaurants?  Totally not knocking that, just trying to identify what worked at Disney and what didn't work in those locales.  Maybe it was the resort element of Disney that appealed, even without the theme park, so pick a resort setting in a locale that you like.

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Yeah before kids our vacations were either cities/museums or hiking. So we were, I guess, trying to keep that going. And now I guess it’s time to pivot to more of a resort type vacation, which isn’t something DH or I would pick otherwise. So I’m sort of at a loss. [/quote]

You could do a staycation so you don't have to worry about sleeping arrangements. Find new hiking trails, new museums, etc.

Or how about try a resort place in Arizona - you can get some hiking in AND still chill by the pool. Just don't over-schedule it. 
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For example: 
Hyatt Regency Scottsdale offers a lot on-site (water park, cultural programs, etc.) and also shuttles for hiking. So your older child can go do something fun while the younger one naps in the room. 
https://www.hyatt.com/en-US/hotel/arizona/hyatt-regency-scottsdale-resort-and-spa/scott

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