On a recent grocery run, I was stopped in my tracks in the produce section by a stunning display of fresh pineapple. Their luscious fragrance caught me first, and those golden beauties were staring me in the face, just begging to go home with me. All the way home, I imagined whipping up some fun tiki drinks, one of my hubby’s favorites. I also considered making a classic pineapple upside-down cake, though I don’t have a great track record with dessert baking. It isn’t for lack of trying; rather, it’s a matter of getting into my own head in a way that messes me up. Still, I’d try it. And then, as I was putting away groceries, a crazy thought hit me.
Could it be a terrible idea to combine the two? Throw a little Comfort du Jour curveball on a pineapple upside-down cake by applying all the tropical flavors of a tiki drink? The magical combination of rum, pineapple, coconut and lime is the flavor equivalent to summer sunshine, and once the idea hit me to include them in a cake— with my good cocktail cherries, of course— well, there was no turning back!

As I gathered up my ingredients to get started, I realized all at once the source of my frustrations with baking sweet treats. It’s me. Yep, it’s my own fault I’m a lousy sweets baker.
But this recipe proved I can break free of that negative self-talk. I just needed to be diligent.
My muse is frequently five or more steps ahead of my mind and my hands, and the exuberance that kicks in when I start making on-the-fly adjustments to a perfectly good recipe is exactly what gets me into trouble. I confuse myself with too many ideas for substitutions, throwing off the ratios that are so necessary for good baking results. It makes me crazy after hours spent in the kitchen on a recipe that seemed so promising at the start.
When I have a crappy result, I inevitably swear off baking— and I am using the word swear quite intentionally. Then, when my persistent muse comes around again, I repeat the whole scenario, sometimes verbatim. But for this cake, I pledged to slow down, chart my substitution ideas more thoughtfully, read the recipe (twice), and truly organize my ingredients into pre-measured amounts (not just put their pantry containers on the counter) to reduce the chances of disaster. And what do you know?— it worked!


My baseline recipe was a skillet version of pineapple upside-down cake that I found on the King Arthur Baking website, my go-to for all things baking. I imagined the wonderful flavors of a tiki cocktail and started rounding up my substitutions.
I wanted rum in the brown sugar topping, and in the cake batter itself. Sweetened flaked coconut would be great in the batter, but that wouldn’t be enough flavor so I’d swap out some of the sugar in favor of this sweet cream of coconut— the same stuff I use in a real tiki cocktail. Key lime juice would spike it with a touch of citrus, but just a touch. Almond extract would play the role of orgeat, the nutty-sweet syrup ingredient that is so distinctively tiki-ish. Our bourbon-drenched cocktail cherries felt more appropriate than the artificially colored bright red maraschinos, and it would be another touch of boozy, grownup candy goodness. And then, of course, my lovely fresh pineapple would be the centerpiece.




With my ingredients measured and in order, following the recipe roadmap was a cinch. The topping was easy, just melting together brown sugar and butter, and then boosting it with a shot of Jamaican rum. I let it get nice and bubbly, then turned off the heat and arranged the pineapple slices. The cherry halves would come later.




I creamed together the butter and cream of coconut, then gradually beat in the sugar. Next came the egg yolks, the flavorings and the flour-milk-flour-milk-flour additions. Alternating those ensures more even blending without overmixing. The egg whites, which were whipped separately, were folded in at the end and I spooned the batter over the brown sugar butter mixture that held the pineapple slices in the skillet.








The baking time was true to the recipe (my toothpick said so), and I inverted the cake onto a serving platter to cool. There’s a sweet spot in timing the inversion from a hot skillet; too soon and the cake may fall apart, too long and the toppings will stick and you’ll be patching them into place. Aim for 15 to 20 minutes for best results, then immediately press the cocktail cherry halves into place while the topping is still warm and gooey. Cool it completely before serving. Waiting to enjoy it was the hard part!




I served my tiki cocktail cake with a dollop of sweetened whipped cream, spiked with more booze of course, as well as a lime twist and a sprinkling of toasted coconut.

So was it worth the trouble? Mostly, yes. The cake was really delicious— definitely boozy, as intended— and the coconut and pineapple were solid co-stars. It had the perfect hint of almond, but the key lime was barely detectable, and next time I would probably just grate a little lime zest over the cake at serving time. The boozy cherries, as much as I love them, got lost a little bit with all the tropical flavors swirling around them, but they were still a nice little nod to a traditional upside-down cake.
The biggest victory for me was seeing the success that resulted from my planning and, for once, I didn’t swear off baking when this was finished. To the contrary, I’m already imagining my next cocktail-to-cake creation. Any suggestions? 😄
Tiki Cocktail Skillet Cake

A few thoughtful ingredient swaps turned a classic cake into tropical tiki territory. You might say that I'm having my cake and drinking it, too!
Ingredients
- 1/2 stick (4 Tbsp.) salted butter, softened
- 3/4 cup light brown sugar
- 2 Tbsp. rum (I used Jamaican dark rum)
- Fresh or canned pineapple rings, drained
- 1 cup all-purpose flour
- 2/3 cup whole wheat pastry flour (or additional all-purpose)
- 1/4 cup sweetened flaked coconut
- 2 tsp. baking powder
- 3/4 tsp. fine salt
- 1 stick (8 Tbsp.) unsalted butter, room temp
- 1/4 cup cream of coconut
- 3/4 cup cane sugar
- 2 large eggs, separated
- 1/2 cup, minus 2 Tbsp. milk (see recipe notes)
- 2 Tbsp. rum (Jamaican again)
- 1 1/2 tsp. vanilla extract
- 3/4 tsp. almond extract
- 1 tsp. key lime juice
- Cocktail cherries, halved (use as many as you have pineapple rings)
Directions
- Preheat oven to 350 F, with rack in center position.
- In a medium bowl, whisk together flours, coconut, baking powder and salt. Set bowl aside.
- Cut unsalted butter into chunks to quicken softening. Separate the eggs, keeping the whites in a large bowl to be whipped. This will be added to the batter just before baking. Combine milk and 2 Tbsp rum in a measuring glass and set aside.
- While all the ingredients are coming to room temperature, prepare the pineapple topping. Melt salted butter in a cast-iron skillet over medium heat. Add brown sugar and whisk until combined and just beginning to bubble. Turn off heat and stir in 2 Tbsp of the rum. Give the skillet a few gentle shakes to settle the mixture evenly in the skillet. Arrange the pineapple slices as desired.
- Cream butter and cream of coconut together in the bowl of a stand mixer, stopping occasionally to scrape down the sides. When mixture is lighter and somewhat fluffy, gradually add sugar, beating and scraping down sides as needed.
- Use an electric hand mixer to whip the egg whites until light and airy but not broken. Set aside.
- Add one egg at a time to the batter, beating until well combined after each. Beat in vanilla, almond and lime juice.
- Alternate addition of the flour mixture and milk as follows: 1/3 flour mixture stirred in until smooth. Next, 1/2 milk mixture. Then 1/3 flour mixture, remaining milk, remaining flour mixture. Scrape down sides and blend as evenly as possible without overworking the batter.
- Give the egg whites a quick whisk again, then gently fold them into the batter, taking care to mix only until the whites are not distinguishable in the batter. Gently spoon the batter over top of the pineapple topping. Use a spatula to smooth out the top.
- Bake for 35 to 40 minutes, until a toothpick inserted in the center comes out clean. Cool for about 15 minutes.
- Run a knife or offset spatula around edges of the skillet to loosen the outer edge of the cake. Invert onto a plate or serving platter. Immediately place the cocktail cherries into the topping, pressing gently to set them into caramelized sugar.
- Cool cake completely. Cut into wedges and serve with a dollop of whipped cream, spiked with cointreau or coconut rum. Sprinkled with toasted coconut.