A deeply chocolatey, incredibly moist bundt cake infused with hot spiced red wine, finished with a red-wine-spiked chocolate ganache glaze. Perfect for the holidays, Valentine's Day, or any night you want a dessert that feels like a celebration.
Before you begin: Preheat your oven to 350°F (177°C). Prepare a 10 to 12-cup bundt pan with cake goop or a generous coating of butter and cocoa powder, getting into every crevice. Bring eggs and buttermilk to room temperature.
In a medium saucepan, combine the red wine, apple cider, honey, orange slices, cinnamon stick, cloves, and star anise. Bring to a gentle simmer over medium-low heat and simmer for 30 minutes, stirring occasionally.
Strain the spiced wine through a fine-mesh sieve. The recipe yields about 1 ½ cups, which is just what you need: 1 cup hot for the cake batter and ½ cup cooled to room temperature for the glaze.
In the bowl of a stand mixer, whisk together the flour, granulated sugar, brown sugar, cocoa powder, baking powder, baking soda, and salt.
Add the eggs, buttermilk, oil, and vanilla extract to the dry ingredients. Mix on low for about 30 seconds until just combined.
With the mixer on low, slowly stream in 1 cup of the hot spiced wine. The batter will be thin. That is correct.
Pour the batter into the prepared bundt pan. Bake at 350°F for 45 to 55 minutes, or until a wooden skewer comes out with just a few moist crumbs.
While the cake is still in the pan, trim off the dome on top with a serrated knife so the cake will sit flat after flipping. Cool the cake in the pan for 15 to 20 minutes, then invert onto a wire rack and let it cool completely.
Make the glaze: combine the milk chocolate chips and butter in a microwave-safe bowl. Microwave in 30-second increments, stirring between each, until smooth. Whisk in the powdered sugar, then the reserved ½ cup of cooled spiced wine. Whisk until smooth and pourable.
Pour the glaze over the cooled cake, letting it drip down the sides. Let set for 10 minutes before slicing.
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Notes
About the wine
Use a fruity, medium-bodied red you would drink. Cab, merlot, zinfandel, shiraz, pinot noir all work.
Avoid "cooking wine" (over-salted) and very dry/tannic wines (bitter when concentrated).
Sweet dessert wines work but reduce the cake's sugar by ¼ cup.
Make-ahead
Spiced wine can be made up to 2 weeks ahead, stored in an airtight jar in the fridge. Reheat the 1 cup portion before adding to the batter and bring the ½ cup glaze portion to room temperature before whisking into the ganache.
Cake can be baked, cooled, wrapped tightly, and stored at room temperature 1 day before glazing.
Storage
Glazed cake at room temperature, covered, for 3 to 4 days. Flavor improves overnight.
Refrigerate up to 1 week. Bring slices to room temp before serving.
Freeze unglazed cake up to 2 months.
Substitutions
Pan: 2 round 8 or 9-inch cake pans (bake 25 to 30 min) or one 9x13 (30 to 35 min) instead of bundt.
Alcohol-free: replace wine with pomegranate juice or grape juice plus 1 tablespoon balsamic vinegar.
Cocoa: Dutch-process works for milder chocolate flavor.
Chocolate chips: semi-sweet for less sweet, more chocolate-forward glaze.
Critical do-nots
Don't use cooking wine. Always use drinking wine.
Don't boil the spiced wine hard. A gentle simmer protects the wine flavor.
Don't underbake. Bundts hide underbaking. Skewer test is non-negotiable.
Don't skip the pan prep. Bundts stick. Use cake goop or butter plus cocoa powder.
Don't add red food coloring to the glaze (unless you want barbecue-sauce vibes). The natural color is prettier.