Wine country trips are frustratingly chaotic -- the only guidance you receive is a time to meet back at the bus, the tasting rooms are thronged with hordes, and chances are that guy from Wings'll ask you to cover for him while he's making his Sandra Oh-face. Sidestep the mob, with So Diego Tours.
Fronted by a San Diego native who started out guiding Segway tours (the future is now!), SoD leverages personal wine-country relationships to improve upon the typical free-for-all by offering what she calls "VIP access at reasonable rates", though of course you'll inevitably drive up the bill with your copious table dances. The itinerary: you're greeted with a pastry and mimosa when you hop on a limo bus in Mission Bay, then you'll roll straight to the reservation-only Briar Rose, where the owner or vintner will fill your glasses liberally, then discuss both the boutique vino industry and ways to take the most away from a wine tasting -- just don't take anything you're not supposed to, or those Temeculans'll put a not-wine barrel in your face. From there you'll head to Falkner for a 3-course wine paired lunch at The Pinnacle Restaurant before heading to their tasting room; after that it's on to Leonesse Winery, where in addition to another tasting-room visit a rep'll guide you on an exclusive barrel-room & vineyard tour -- so you'll learn where your wine came from even as you forget where you is
As for the bus itself: they'll take requests for the iPod playlist, and guests are permitted to BYO wine, beer, and champagne, though there is a $300 cleanup fee for anyone who physically can't handle their suds -- though if that's happening at your age, your wings should be clipped.