I decided to skip right over the savoury courses of your holiday dinner and suggest some dessert pairings for the popular sugary parts of the menu. At the same time, I wanted to veer from the stalwarts of sweet pairings (foie gras and Sauternes, Port and chocolate, etc.) Desserts served after the big meal vary greatly from household to household, but I've taken a few stabs below.
The Cookie Spread. In my family, post dinner usually means a platter of home baking spread across the table with a pot of coffee and a bottle of Grand Marnier (a pretty good pairing, actually). I'm thinking about sugar cookies, gingersnaps, and biscotti. A nice amaro or Italian digestif like Amaro Montenegro will cover a lot of ground. Icewines are fantastic with sugar cookies and biscotti (check out the Luckett Vineyard 2010 Isolde Vidal Icewine). Also, a PX Sherry will complement much of the baking that contains nuts and molasses flavours (Osborne makes one that is cheap and delicious).
Fruit Cake. Is there another dessert loathed as much as the fruit cake? But when it's made well and isn't baked to sawdust, it has the potential for greatness. This is where the vintage port you've been saving will come in handy. Also Banyuls or Rasteau. For something different, I love the idea of Elephant Island's 2013 Apricot Dessert Wine.
The Old Fashioned Apple Pie. There are plenty of options here, as many great dessert wines naturally carry those complementary flavours of baking spice and caramelized apples. For a spin on an apple pie, but with similar flavours, check out Jamie Oliver's Tart Tatin recipe. While sweet Chenin Blanc from the Loire like Domaine des Baumard's Quarts de Chaume will work nicely, it's hard to beat the pairing of sweet Riesling with baked apples. Check out the delicious and well-priced Tawse 2013 Riesling Icewine.
Creme Brulé. Custard and vanilla with the fresh caramel flavours of burnt sugar? This is a classic Sauternes pairing. For something different, look for Passito di Pantelleria, a delicious dessert wine made from dried Zibbibo grapes (aka Muscat) from the Italian island Pantelleria. Or, heading back to Elephant Island, their 2013 Crab Apple Wine has such a pure, concentrated flavour, with tart acidity.
Jake Skakun is a writer and sommelier from Vancouver, currently living in Toronto. He can be found most days pulling corks and twisting caps at the Black Hoof. He Tweets and Instagrams @jakeskakun.