The secret: Plan the days so he's not left figuring them out by himself. At my house, when vacation rolls around, I put together a kick-booty schedule studded with mommy-kid time.
A couple mornings a week, my two girls and I take a trip to the museum or park; other days, we might pull out a favorite game. Afternoons, they play together while I work; later, we reconvene for dinner and maybe a walk. I also import their friends a few afternoons a week. The best part: Other moms return the favor by having my kids over, taking me out of the picture, at least for a few hours.
Ask Mom Squad expert Denene Millner your trickiest parenting questions at Parenting.com/momsquad.