With Milk Chocolate:
Milk chocolate and Tawny Port is a delightful duo. The creamy, caramelized notes in Tawny Port compliment those same flavors in a handful of Regular or Peanut M&M’s, a bowl of Milk Duds, Malted Milk Balls, or even Reese’s Peanut Butter Cups. Malmsey Madeira is another delicious pairing option for similar reasons. Malmsey Madeira’s toffee notes are particularly great with a Skor Bar, a Snickers, Reese’s Peanut Butter Cups or almost anything involving milk chocolate and nuts. Moscatel Sherries, and sweet Pedro Ximinez (aka PX) wines from southern Spain, are also excellent with milk chocolate. These wines often taste of dried figs and caramel and are delightful with Raisinettes.
With Dark Chocolate:
Dark chocolate can handle a wine with more whimsy—and more fruit. If you’re feeling sassy, dark chocolate pieces of say, Valrhona bittersweet baking bits, are surprisingly great with Sparkling Shiraz from Australia. The effervescence is refreshing with dark chocolate’s deeper notes, and Shiraz’s black pepper and black raspberry flavors are natural accompaniments for dark chocolate. Recioto del Valpolicella, a sweet wine from Italy’s Veneto region made from Corvina and Rondinella grapes (that have been dried for months on straw mats before they’re fermented) is a rich yet bright wine that tastes of dark-chocolate-covered Bing cherries.
With Chocolate Chip Cookies:
A general guideline is to ensure that your wine is sweeter than your food. (A famous mismanaged pairing involves Champagne and wedding cake. That is not a match made in heaven!) Wines that go well with chocolate chip cookies need to be sweeter than the cookies themselves. A Tawny Port and a Malmsey Madeira (the sweetest style of Madeira made from the Malvasia grape) both pair deliciously with chocolate chip cookies—the flavors naturally highlight chocolate bits. (Plus, Madeira is great to have around the house as it never goes bad!) If you’re in the mood for a more refreshing pairing, try a Tokaji from Hungary. This famous botryticized sweet wine tastes of caramel and slightly-roasted apricots.