There are only a few things about most alcoholic drinks that are bad for you: the alcohol, the sugar, the gluten. Therefore, avoiding or minimizing these things is what leads to the best choices. After much trial and error, here's what I've found to be the healthiest.
Sangria. Everyone knows that a little red wine is good for you. Well, if you add fruit and skip the brandy, it's even better.
Wine spritzer. These are great for hot summer days, when you want to drink a lot of fluid. Just add a lot of soda water/seltzer/club soda to wine (red or white), good amount of lemon, a splash of pomegranate juice, all over ice, and you've got yourself a drink.
Norcal margarita. A Norcal man myself, I have a great deal of affection for this invention by none other than Robb Wolf. It's just 100% agave tequila, plenty of fresh squeezed lime, and splash of soda water, but it's scientifically formulated to keep your blood leaning alkaline and to blunt the insulin response.
Gluten-free beer. Hard to find, but it's out there and doesn't taste bad at all. Brands include St. Peter's, Bard's, and Red Bridge.
P.S. I built that wine rack myself, all paleo. Literally carried that log out of the woods. Fits into the 'hobby' part of my exercise pyramid :)