I'm not much help as far as family fun but since you mentioned wine, I can give you pointers on where to go winerywise (I just got back from a trip in which I visited over 17 wineries in the area.)
Basically most wineries on Black Sage Road (in between Oliver and Osoyoos paralell to Hwy 97) are gold as this has got to be the best place to grow some of the bold red wine grapes. My favorites include Burrowing Owl, and Desert Hills. Actually in Osoyoos N'Mip winery is usually a good place to visit and there's a Desert interpretive center there as well.
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