Pineapple Upside Down Cake

Pineapple Upside Down Cake is a classic dessert where pineapple and maraschino cherries are placed at the bottom of a baking pan before the batter is added. After the cake is baked and cooled, the pan is then inverted so that the fruit is on top. The best part, in my opinion, is that the sugars in the fruit caramelize while in the oven, resulting in a delicious, indulgent, caramel syrup that covers the cake.

To mirror those flavors in a cocktail, I used caramel flavored vodka, pineapple juice, and just a hint of amaretto to add depth.



  1. Chill martini glass by filling with ice water. Set aside.
  2. Fill mixing glass with ice.
  3. Pour in all ingredients.
  4. Shake mixture vigorously until shaking can frosts over.
  5. Discard ice water from martini glass.
  6. Strain mixture into chilled martini glass.
  7. Garnish with a maraschino cherry.

This dessert cocktail is not particularly strong, so if you prefer something with a little more kick, substitute the simple syrup for more vodka!

If you're in the mood for a pineapple upside down cake shot, the above recipe will yield three to four 1.5 oz shots. To represent the cherry, use a small amount of grenadine or maraschino syrup. Into each shot glass, pour a few drops of the syrup slowly over the back of a spoon, and the syrup will sink to the bottom. I would advise against dropping actual cherries into the shot glasses because, well, nobody likes choking.