Pineapple upside down cake has been a cherished dessert for generations, with fond memories going back before the 1950’s. We decided it was about time to give the recipe a bit of a facelift while still keeping true to the its roots. What we ended up with is a cake that’s fruity, bold, and more flavorful than ever. A melody of allspice and bay leaves give this upside down cake a vibrant Caribbean flair. Although, the true star of the show here is long pepper. The pine cone-shaped spice is gingery and has notes of cardamom and black pepper. This flavor in the gooey caramel at the bottom layer of this cake is simply other-wordly. Buttery, fluffy, fruity, spicey — this is everything you’d want wrapped up in one drool-worthy dessert!
Caribbean Pineapple Upside Down Cake
- 2 cups pineapple, thinly sliced
- 12 Luxardo or maraschino cherries
- 1/2 cup (1 stick) butter, cold
- 1/2 white sugar
- 2 eggs
- 1 cup sour cream
- 1/2 cup vegetable oil
- 1 vanilla bean
- 1/2 teaspoon salt
- 1 teaspoon Jamaican allspice, ground
- 1-1/2 cup all-purpose flour
- 1 teaspoon baking powder
- 1/4 teaspoon baking soda
- Preheat the oven to 350°. Pan spray an 8-inch baking pan and line it with parchment paper.
- Arrange the fresh pineapple slices along the bottom of the pan in preferred design. We shingled the pineapple slices neatly and filled in any holes with maraschino cherries. This layer will end up being the presentation side of the cake. Once the fruit is arranged, thinly slice the cold butter and sprinkle it on top of the fruit. Set aside.
- Meanwhile for the caramel sauce add the brown sugar, butter, water, salt, bay leaf, long pepper and cinnamon in to a small saucepan and cook on medium high heat for 5 minutes. The mixture should appear saucy and smell nutty and caramel-like. Once the sauce has thickened and slightly deepened in color, drizzle it evenly over the arranged fruit. Set aside.
- In a large bowl add the sugar, eggs, sour cream, vegetable oil, vanilla bean, and allspice — whisking together until smooth and the mixture has come together. Slowly add in the flour, baking powder, and baking soda until the batter is smooth. Evenly pour the batter using a spatula onto the prepared fruit in the pan. Spread the batter to create an even layer. Bake the cake for 30-40 minutes or until a toothpick inserted in the center comes out clean. Once baked, lay a plate or pan a little larger than the cake pan over the finished cake and flip it onto this serving plate. Peel off the parchment paper and blow torch or broil on high for a couple of minutes for extra caramelization if needed. Serve immediately or cover and refrigerate for up to 3 days.
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When preparing the vanilla bean, lay it flat and flatten the bean with the back of your knife. For seed removal, use a sharp knife to slice the vanilla bean down the middle, lengthwise, creating two long halves. Using the backside of the knife, run down the length of each split open pod and scrape out the seeds. Use the seeds for the recipe.
It is highly suggested to keep the vanilla pod shells and use them in the future for a custard infusion, like ice cream. Another fantastic use is to infuse your own vodka or bourbon with these pods. We made incredible French Martinis with our own vanilla infused vodka, check it out here.