Pairing Chocolate and Wine
Approach wine and chocolate tasting the same way you would any other tasting: start with the light options and move your way through the spectrum to the darker, heavier flavors. In general, the sweeter the chocolate the sweeter the wine should be, and the lighter the chocolate (consider flavor, not just color) the lighter the wine. Full-bodied, heavy red wines will best complement dark and bittersweet chocolates, while a light riesling or dessert wine will more likely pair well with a sweet milk chocolate. Many think champagne is wonderful with white chocolate.
One other aspect to think about when considering which wines and chocolates will go well together is each of their predominate and underlying flavors -- you'll get very different results when you choose varieties that have similar flavors versus those with very contrasting ones.