It's real - the idea is that young Jewish Obama supporters visit their grandparents in Florida over Columbus Day weekend, and try to talk these (often very involved, often very Democratic) people out of their doubts about Obama - mainly convinicing them he's not Muslim.
At the very least, they would have visited their grandparents. (This is actually an argument they use for going - you'll make your grandparents happy.) I mean, on their website, thegreatschelp.com, the answer to "How do I go?" is, "Call your grandparents and tell them to get the couch ready." If you can't go, at least call your grandparents.
Will this help the Obama campaign? Who knows. It certainly couldn't hurt it.