There are lots of ways to go right while picking out a wine to finish off a meal, but there are also some ways to go wrong. To guard against that, there is one rule of thumb that should always be followed when scanning your local wine shop for the perfect sipper: The wine being chosen should always be sweeter than the actual dessert, according to Dan Rivas, general manager at Bank & Bourbon, located in the Loews Hotel in Philadelphia, Pennsylvania.
“It can be helpful to try and match your wine and dessert based upon their similar flavors,” Rivas says. “One example would be a sparkling Moscato D’asti which has notes of fresh peach and pear and slight residual sugar which would match up beautifully with any dessert that incorporates fresh fruit and lavender.”

Chocolate treats, however, can be a bit tricky. Rivas says that starting your search with a fortified wine, such as Port or Madeira, is a catchall recommendation. However, you can get more specific depending on the type of chocolate that is in the dessert.
“With milk chocolate which is typically half chocolate and half milk, a ruby Port would be an excellent choice because it is going make for a more fruit and spice driven pairing. With dark chocolate, a tawny Port or Pedro Ximenez sherry pair wonderfully because they will add nutty and raisin flavors to the dessert. When pairing with white chocolate, some recommendations that tend to pair well are ice wines which will accentuate the dessert with notes of pineapple, and Brachetto D’acqui which will deliver notes of crème and raspberry,” he explains.

But, when all else fails and you’re at a loss, go for the sparkling.
There is nothing better than a good sparkling wine paired with a good cupcake. Something about the bubbles I feel just enhances the flavors.

Thanks to New York Wine and Grape Foundation May 2019 Newsletter