You know you're deep into the holiday cheer when you open the door in the morning and find brownies and cookies on your doorstep. Let the poundage begin! Whether you like it or not, holiday sweets are unavoidable. So, all the better to make them palatable by drinking the right kinds of things with them. While I'm not a prolific drinker of dessert wines, they do have their time and place. So there are three versatile types of sweet wines to keep around to cover most of your holiday needs. Just remember the basic fact of pairing sweet things: The wine should always be sweeter than the dessert. If you don't follow that, neither dessert nor wine will taste good. If you do follow it, it's all good!
Port goes with chocolate--fudge, brownies, pies, you name it. To make it go even better, choose a nice ruby port (that's the category that looks like dark red wine) and a semisweet dark chocolate. Now you don't have to use a super expensive vintage port. There are other styles that are easier to drink and are not too pricey. I'm a fan of the Smith Woodhouse Late Bottled Vintage 1995. It's 14 years old, but is bottled late so it's super round and balanced and only $30.
This is what you want with fruit desserts, butter coockies, lemon cakes and anything a little lighter. It's a category of sweet white wines from France, known for their honeyed complexity and peach-apricot deliciousness. The most expensive is the famed Chateau d'Yquem, but there are lots of good ones around for much cheaper, such as this one.
From the island off of Portugal out in the Atlantic comes one of the most versatile sweet wines in the world. What makes Madeira so exciting is that it can be dry, off-dry or sweet, but good ones always have this thrilling core of acidity that shoots through them like a neon arrow, keeping them as refreshing as they are rich and powerful. For desserts, they're wonderful with anything nutty, toffee, or caramelized and can also go well with reach creamy dishes and baked fruits. For a sweet, but not too sweet, version, look for a kind called Malmsey, like this 10 year old version from Blandy's.