Like many people nowadays, I generally prefer the purer flavors of dark chocolate to milk chocolate. But counterintuitively, I found that the light sweetness of milk chocolate was more versatile with a wider range of wines than the darker chocolates, which have a distinct bitterness that, while welcome on its own, can clash with a wine that’s not equipped to handle it.

Regardless of the chocolate itself, the wines that go with it best share two particular characteristics: They are intensely sweet, and they have good acidity, a quality that, despite the sweetness, lifts the wine and refreshes the palate, leaving you ready and eager to eat even more chocolate.

The wines most often associated with chocolate are port and Madeira. The two are frequently uttered in the same breath, yet I by far preferred Madeira with each type of chocolate. Madeira, from the Portuguese island of Madeira, can range from dry and light to rich and very sweet. The sweetest Madeiras, generally made from the malvasia candida grape and labeled “malmsey,” are what you want with chocolate. Bual Madeiras, which are slightly less sweet, were overwhelmed, but chocolate and malmsey indeed was a lovely match.

Blandy’s 5-Year malmsey, a wine aged a minimum of five years, is a good entry-level Madeira and costs about $20 to $25. Even better is Blandy’s 15-Year Madeira, for $35 to $40, which had a beautifully bright, refreshing flavor that was superb with chocolate. Best of all would be vintage malmsey, or one of my favorites, New York Malmsey Special Reserve, a bottling from the Rare Wine Company made in the style of Madeiras from the 18th and 19th centuries. It was almost kaleidoscopic in its complexity yet remained deliciously refreshing. It can be found for around $60.