Pineapple Upside-Down Cake Recipe

This Pineapple Upside-Down Cake recipe combines sweet caramelized pineapple, buttery brown sugar topping, and a tender vanilla cake for a dessert that is both nostalgic and elegant. Featured on Dine Your Sign, this individual-sized version of the classic upside-down cake is finished with flaky sea salt and creamy crème fraîche, creating a perfect balance of sweetness, richness, and freshness.

The Inspiration

On this Gemini-inspired episode of Dine Your Sign, Chef Siobhan Detkavich celebrates the zodiac sign known for its playful nature, adaptability, and tendency to see things from multiple perspectives. Ruled by Mercury, Gemini often enjoys putting a fresh spin on familiar ideas, making the Pineapple Upside-Down Cake a fitting tribute.

This dessert literally turns tradition on its head. The fruit begins at the bottom of the ramekin but becomes the beautiful top layer once inverted. The transformation mirrors Gemini’s ability to approach life from different angles and find excitement in unexpected places.

Ingredients

• 1 cup (240 ml) plus 2 tablespoons (30 ml) unsalted butter, room temperature, divided (plus more for ramekins)
• ½ cup (120 ml) brown sugar
• 6 slices fresh pineapple, about ¼ -inch (6 mm) thick
• 1 cup (240 ml) sugar
• 1 ¾ cups (410 ml) cake flour
• 1 teaspoon (5 ml) vanilla extract
• 1 ¾ teaspoons (23.25 ml) baking powder
• ½ teaspoon (1.25 ml) salt
• 2 large eggs, beaten
• 2/3 cup (160 ml) 2% milk
• Flaky sea salt, to garnish
• Crème fraiche, to garnish

Special equipment

• 6 x 10 fluid ounce (300 ml) ceramic ramekins (round, 4 ½-5-inch x 2 ½-inch/11.25-12.5 x 5.75 cm)

Method

• Preheat oven to 350 F (175 C).
• Generously butter ramekins and arrange on a baking sheet.
• Melt ½ cup (120 ml) butter in a small saucepan. Remove from heat and stir in the brown sugar.
• Using a 4 ½-5-inch (11.25–12.5 cm, to match the ramekin) round cutter, trim pineapple slices to fit into the bottom of each ramekin.
• Carefully pour enough butter/brown sugar mixture into each ramekin to evenly cover the bottom.
• Use a small round cutter to remove the core from pineapple rounds, and place one round in the bottom of each ramekin.
• In the bowl of an electric mixer fitted with a paddle, combine the remaining butter, sugar, and vanilla extract. Beat until light and fluffy.
• Add the eggs, 1 at a time, beating well after each addition.
• In a bowl, sift together the flour, baking powder, and salt.
• Gradually add flour mixture and the milk to the mixer with the butter-egg mixture, alternating, in stages, beating between each addition. Continue until batter has been formed.
• Divide the batter evenly between the prepared ramekins to a depth of about 1 inch (2.5 cm).
• Bake for 30 minutes, until the top is firm, and a tester inserted in the middle comes out clean.
• Let cakes cool 1 minute before inverting onto serving plates.
• Sprinkle sea salt over the cakes. Place a quenelle (spoonful) of crème fraiche beside each cake and serve immediately.

Serving Suggestions

This Pineapple Upside-Down Cake is an excellent dessert for dinner parties, family gatherings, brunches, birthdays, and holiday celebrations. Its bright tropical flavor makes it especially appealing during spring and summer, though it can be enjoyed year-round.

Serve the cakes warm with crème fraîche as suggested, or pair them with vanilla bean ice cream, whipped cream, or mascarpone for additional richness. Fresh berries can add color and acidity, while toasted coconut flakes create a tropical finishing touch.

For beverages, pair this dessert with coffee, espresso, black tea, dessert wine, or a tropical cocktail. The caramelized pineapple flavors also complement rum-based drinks particularly well.

Final Thoughts

This Pineapple Upside-Down Cake recipe is a celebration of classic baking, vibrant fruit, and playful presentation. Featured on Dine Your Sign and inspired by Gemini’s love of turning expectations upside down, it transforms a beloved retro dessert into an elegant modern treat.

The combination of fresh pineapple, buttery caramel, tender vanilla cake, flaky sea salt, and creamy crème fraîche creates a dessert that feels both comforting and sophisticated. Every bite delivers sweetness, richness, freshness, and balance, making it a standout finale for any meal.

Find more recipes from Dine Your Sign here!

Follow us on Instagram and YouTube for behind-the-scene footage and exclusive content!