Piña Colada Pineapple Upside Down Bread Pudding

Food mash-ups have been all the rage in recent years. Some of them are brilliant creations, like the Korean taco or spaghetti lasagna, while others have been frightful like that crazy ketchup and mustard cake video that’s gone viral. But I’ve created my very own mash-up and let me just tell you…it’s a winner.

My husband’s favorite dessert is pineapple upside down cake, and my favorite dessert is bread pudding. With all these food mash-ups, I thought if he and I pair so well together then surely so would our favorite desserts. So I came up with this Piña Colada Pineapple Upside Down Bread Pudding. Which is a mouthful, so try not to say it too much. Instead, reward your mouth with a taste of this!

My thought process behind this was that pineapples have that tropical flavor and that piña colada would be the perfect complement to that. It’s truly a perfect pairing! I topped the bread pudding with a rum-spiked coconut syrup (the very same coconut syrup from my post 2 weeks ago about my sweet potato coconut waffle). It added that extra echelon of awesomeness I was going for.

Let me tell you…this dessert is next level all the way. It turned out smooth and moist without being wet and soggy. And while it was sweet, it wasn’t cloying. I found it to be the perfect balance, and with summer almost here, this dessert mash-up is the ultimate vacation for your taste buds!

Piña Colada Pineapple Upside Down Bread Pudding

1 cup Piña Colada (you can use your favorite Piña Colada or use the Piña Colada recipe below) 
1/2 cup milk
3/4 cup half and half
4 eggs
1   13 oz loaf of Challah, cut into 1 – inch pieces
1 tsp coconut extract
1/2 cup + 2/3 cup light brown sugar divided
1/4 cup granulated sugar
1   1/2 tsp vanilla extract
2 tsp coconut extract
6 tbsp + 1/3 cup unsalted butter (melted)
1   20 oz can pineapple slices in  juice


  1. In a small bowl combine 2/3 brown sugar and 1/3 butter until blended. Spray oil in eight – 8 oz ramekins; set aside.
  2. Spoon into eight – 8 oz ramekins. Drain pineapple, reserving the juice. Place a slice of pineapple into prepared cup.
  3. To make the bread puddings: Preheat oven to 350 degrees with rack set in the lower third of the oven.
  4. Place bread in a large bowl.
  5. Mix 1/4 cup sugar, and 1/2 brown sugar in a bowl. Pour half and half, milk, Piña Colada, melted butter, and 4 beaten eggs, coconut extract, and vanilla extract in with the sugar.
  6. Pour the egg mixture over the bread, tossing until well combined.
  7. Evenly divide bread mixture between prepared ramekins, making sure liquid covers the bread.
  8. Bake for 40 minutes until the bread puddings are golden brown
  9. Serve with coconut syrup (the very same coconut syrup from my post 2 weeks ago about my sweet potato coconut waffle

Pina Colada

1/4 cup of white rum
1/4 cup of amber rum
1/2 cup of cream of coconut
1 cup of pineapple juice
1 (13.5 oz) can of coconut milk
1 cup of Pina Colada mixer


Mix all of the ingredients together

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