My board game and other crews don't drink as much anymore, so I don't get to make cocktails very often. :( But here are my two favorites for the season (and they're both sweet as fuck, though):
Coquito
1 can evaporated milk
1 1/2 cups white rum (though I think just about any tastes pretty good in it)
1 can sweetened condensed milk
1/8 tsp ground nutmeg
1/4 tsp cinnamon plus dusting for serving
1 tsp vanilla extract
2 cups coconut cream (one big can or 2ish smaller ones)
cinnamon sticks for garnish
You can lessen the rum if you don't want a warm kick.
Blend/wisk everything together, and refrigerate for at least 2 hours (I think it's better chilled at least overnight). Probably you want to start with a SMALL glass first. And you can double/triple the recipe really easily as well as experiment with the ratios.
North Pole Cocktail
Found this recipe a few years ago and uh...accidentally got my youngest kiddo's toddler teacher drunk off her ass at an adults only Christmas party, if you like gingerbread flavor they go down really quick. Probably it'd taste really good even without the molasses but I've only made it with it in there.
4 oz vodka
2+ oz kahlua
4 Tbsp chocolate syrup
1 tsp vanilla extract
3 tsp molasses
1/8 tsp ginger
1/2 cup heavy cream
whipped cream, crushed peppermint candies, and crushed gingerbread cookies for garnish.
In a cocktail shaker combine vodka, kahlua, chocolate, vanilla, molasses and ginger, shake until well combined. Add ice and shake again. Strain into 4 glasses. Top off each glass with heavy cream. Dollop with whipped cream and use crushed peppermint candies and/or cookies as garnish.