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Decadent Chocolate Lollipop Cake for Valentine's Day

Create the ultimate dessert experience with this show-stopping Chocolate Lollipop Cake. Featuring layers of moist, rich chocolate cake infused with red wine and topped with tender poached pears, it's a truly decadent treat. This recipe is the perfect way to craft a memorable Valentine's Day Lollipop dessert for someone special.
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Course: Cake, Dessert, Valentine's Day
Cuisine: American
Keyword: Chocolate Pear Cake, Ganache, Lollipop Cake, Red Wine Chocolate Cake, Valentine's Day Lollipop
Prep Time: 40 minutes
Cook Time: 30 minutes
Cooling Time: 30 minutes
Total Time: 1 hour 10 minutes
Servings: 16 servings
Calories: 345kcal

Ingredients 

For the Red Wine Poached Pears

  • 3-4 Bosc pears firm
  • 1 cup water
  • 1 1/2 cups red wine a dry red like Merlot or Cabernet Sauvignon
  • 1 teaspoon ground cinnamon
  • 3-4 whole cloves or 1/4 teaspoon ground cloves

For the Chocolate Cake

  • 2 large eggs
  • 1/2 cup full-fat coconut milk from a can
  • 1 teaspoon apple cider vinegar
  • 11 tablespoons unsalted butter
  • 1 1/2 cups coconut sugar
  • 1/2 cup red wine
  • 1/2 teaspoon pink salt or regular fine sea salt
  • 1/2 cup dark chocolate 85% cacao, chips or a bar broken into small pieces
  • 1 tablespoon vanilla extract
  • 1/2 cup unsweetened cocoa powder
  • 1 cup all-purpose flour gluten-free or regular
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda

For the Chocolate Ganache

  • 2/3 cup dark chocolate chips
  • 1/3 cup full-fat coconut milk or heavy whipping cream
  • 2 tablespoons reserved spiced wine from poaching the pears

Instructions

  • Prepare the pears by peeling, coring, and halving them. In a saucepan, combine the pears with water, 1 1/2 cups of red wine, cinnamon, and cloves. Bring the liquid to a boil, then reduce the heat to a simmer for 20 minutes until the pears are fork-tender.
  • Remove the poached pears from the saucepan and set them aside to cool. Continue simmering the remaining wine mixture until it has reduced and thickened into a sauce. Set aside 2 tablespoons of this spiced wine sauce for the chocolate ganache later.
  • Preheat your oven to 350°F (175°C). Thoroughly grease two 9-inch springform cake pans with butter or oil and set them aside.
  • Combine the 1/2 cup of coconut milk and apple cider vinegar in a small bowl and let it sit for at least 5 minutes to curdle. In a separate bowl, lightly whisk the two eggs.
  • Melt the unsalted butter in a separate saucepan over low heat. Whisk in the coconut sugar, then remove the pan from the heat. Stir in the 1/2 cup of red wine and pink salt. Immediately add the dark chocolate pieces, stirring constantly until the chocolate is fully melted and the mixture is smooth. Finally, whisk in the vanilla extract.
  • Temper the eggs by slowly pouring about one-third of the warm chocolate mixture into the whisked eggs while mixing continuously. Once combined, pour the tempered egg mixture back into the saucepan with the rest of the chocolate and stir well.
  • Pour the chocolate mixture into a large mixing bowl. Add the curdled coconut milk mixture, cocoa powder, all-purpose flour, baking powder, and baking soda. Mix until the batter is just combined, being careful not to overmix.
  • Divide the cake batter evenly between your two prepared cake pans. Slice the cooled, wine-poached pear halves into quarters and arrange them in your desired lollipop-style design on top of the batter.
  • Bake for 20-30 minutes, or until a toothpick inserted into the center of the cakes comes out clean.
  • Prepare the ganache while the cakes are baking. In a small saucepan, gently heat the dark chocolate chips and 1/3 cup of coconut milk over low heat. Whisk continuously until the chocolate is melted and smooth. Remove from the heat and whisk in the 2 tablespoons of reserved spiced wine sauce.
  • Remove the cakes from the oven and allow them to cool completely in their pans before releasing. Place one cooled cake layer on a serving platter, drizzle with some chocolate ganache, then carefully place the second cake layer on top. Pour the remaining ganache over the entire cake, letting it drip down the sides for a stunning finish.

Equipment

  • Saucepan
  • 9-inch springform cake pans
  • Mixing bowls
  • Whisk

Notes

For the best flavor, use a dry red wine like a Cabernet Sauvignon or Merlot. You can also experiment with other firm pears such as Anjou if Bosc pears are not available. Ensure the cake is fully cooled before frosting to prevent the ganache from melting.

Nutrition

Calories: 345kcal | Carbohydrates: 45g | Protein: 4g | Fat: 18g | Saturated Fat: 10g | Cholesterol: 55mg | Sodium: 150mg | Potassium: 210mg | Fiber: 4g | Sugar: 30g | Vitamin A: 450IU | Vitamin C: 1.2mg | Calcium: 45mg | Iron: 2.5mg