1 cup boiling water
1 (3 ounce) package cherry-flavored gelatin (such as Jell-O®)
4 fluid ounces white rum
3 fluid ounces creme de cacao
1 fluid ounce vodka
16 maraschino cherries
1 cup whipped cream
1 tablespoon chocolate syrup, or to taste
Combine boiling water and gelatin together in a bowl; stir until dissolved. Mix white rum, creme de cacao, and vodka together in a bowl. Pour alcohol mixture into gelatin mixture.
Place 1 maraschino cherry into each shot glass; fill with gelatin mixture. Chill in the refrigerator until set, 8 hours to overnight. Remove from refrigerator; top with whipped cream and chocolate syrup.