This is the first real summer-y dessert I made this year and let me just say, this thing just embodies summer. The perfect ending to a cookout or pool party, and if you're not up to the boozy version, just leave out he alcohol for a delicious family friendly treat. With my set of popsicle molds this makes about 6 pops. Depending on your molds (or paper cups and popsicle sticks if you don't have molds) you could make more or less. It's really up to you to make this how you want. —Taylor Ayral
ripe pineapple, cubed
zest of one lime
golden rum (or your choice of alcohol, optional)
Combine the Pineapple, Lime Zest, Rum, and half the Sugar in the work bowl of a food processor. Process until everything is combined into a slush.
Fill your popsicle molds 1/2 way with the Pineapple mixture, place in the freezer for 40 minutes while you make the Cherry. You want the Pineapple layer to be solid enough that it won't mix with the Cherry. If you don't care about that, you can wait less time.
In the cleaned food processor bowl, combine the Pitted Cherries, Vodka, and remaining half of Sugar. Process until everything is combined into a slush.
Once the Pineapple is solid enough for your liking, fill popsicle molds the rest of the way up with Cherry mixture.
Place the sticks/tops on the popsicle mold, and put in the freezer until solid, ~6 hours or overnight.