From Stacy Slinkard,
Your Guide to Wine.
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Some say it can’t be done, pairing wine with chocolate, but if you have the right wine to complement the right chocolate it can be a match made in heaven! Whether you are pairing a delicate white chocolate or a lively dark chocolate with wine, there are a few pairing tips to keep in mind.

Tips for Successfully Pairings Wines with Chocolate

Rule #1, the wine should be at least as sweet, if not a touch sweeter, than the chocolate you are serving it with. Otherwise, the taste may quickly veer towards sour.

When pairing wines with chocolate, your best bet is to match lighter, more elegant flavored chocolates with lighter-bodied wines; likewise, the stronger the chocolate, the more full-bodied the wine should be. For example, a bittersweet chocolate tends to pair well with an intense, in-your-face California Zinfandel.

Similar to “formal” wine tasting, if you will be experimenting with several varities of chocolates, work from light to dark. Start with a more subtle white chocolate and end on a dark or bittersweet chocolate.

White Chocolate Wine Suggestions

White chocolate tends to be more mellow and buttery in flavor, making it an ideal candidate for a Sherry (try Manuel de Argueso Pedro Ximinez $18), a Moscato d'Asti (try Michele Chiarlo Moscato d'Asti 2005, $12), from Italy’s Piedmont region offers a hint of carbonation, or an Orange Muscat (try Ventana Vineyard's Muscat d'Orangefor $18). The Sherry and Moscato d’Asti will pick up the creaminess of the chocolates and the Orange Muscat will pick up any fruit tones present.

Milk Chocolate Wine Suggestions

Pinot Noir (Rex Goliath Pinot Noir $9) or a lighter-bodied Merlot (try Hogue or Columbia Crest) will complement a bar of milk chocolate, a creamy chocolate mousse or chocolate accented cheesecake. Rieslings, Muscats (try Bonny Doon's Muscat Vin de Glaciere 2004 or the 2005 Bonny Doon "Vin de Glaciere" Muscat for $15) or dessert wines tend to hold up well to mild milk chocolates.

Dark Chocolate Wine Suggestions

Dark or bittersweet chocolates need a wine that offers a roasted, slightly bitter flavor itself, with perhaps a hint of its own chocolate notes. Cabs and Zinfandels have a history of perfecting the dark chocolate match, resulting in an unparalleled tasting combination. A Cabernet Sauvignon or a Zinfandel (try Grgich Hills Zinfandel 2005, $30) will more than fill your chocolate pairing expectations.