Heat sugar and 1/2 cup water in a saucepan over low heat; cook and stir until sugar is dissolved, about 2 minutes. Remove from heat and stir in almond extract.

Pour pineapple orange concentrate and limeade concentrate into a large pitcher; stir in 1 1/2 cups water. Stir in dark rum, light rum, and almond simple syrup.

Place 1 pineapple tidbit and 1 maraschino cherry half in the bottom of each ice pop mold. Pour in rum mixture and freeze for at least 12 hours.