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Pineapple Upside-Down Jello Shots

Yield: 12


  • 12 2.5 oz plastic Jell-O shots cups
  • 12 maraschino cherries with stems
  • 2 cups pineapple juice
  • 2 Tablespoons granulated sugar
  • 2 envelopes Knox unflavored gelatin
  • 1/2 cup vodka - chilled
  • 2 Tablespoons grenadine
  • 1 teaspoon vanilla extract
  • Optional - splash of Amaretto in each cup


  • Cut off the the bottom of each stemmed cherry and place in the plastic cups. Place the plastic cups inside a mini muffin tin or place on a cookie sheet.  Set aside the bottom pieces for later use.
  • Add the pineapple juice to a small saucepan and warm the juice under medium/low heat for 5 minutes, stirring occasionally.  Do not allow the juice to boil.  Remove from heat and whisk in the sugar and unflavored gelatin.
  • Return to medium heat and whisk constantly until the gelatin is completely dissolved (about 2 minutes).  Remove from heat.
  • Add the chilled vodka and stir well.
  • Divide the pineapple vodka mixture evenly into 2 bowls.  Add the grenadine to one bowl (it will make the juice a red-orange color) and pour over the cherries in each plastic cup, filling each cup 1/2 of the way. Optional - add a splash of amaretto to each cup.  Set aside the remaining bowl of juice for Step 7.
  • Chill for 30 minutes to allow the gelatin to "set."
  • Once chilled, pour the remaining pineapple vodka mixture on top of the orange layer and return to the refrigerator.  Chill for an additional 30 minutes.
  • Take the bottom pieces of the cherries and poke a hole into the middle of each piece.  Once the pineapple upside down Jello-O shots are "set," slide a cherry piece over each stem and allow each piece to lay on top of the yellow layer.
  • To pop them out, set the cups in warm water and they will pop right out!