To make the syrup, grill the pineapple wedges until lightly charred. Reserve about one-third of the grilled pineapple wedges for garnishes and add the rest to a pot with brown sugar and water. Bring to a boil, reduce heat and simmer for 5 minutes. Remove from heat, cool to room temp then strain and chill. The syrup can be made ahead of time and stored, refrigerated, for up to 10 days.
In a shaker or mixing glass, combine the pineapple syrup, rum and bitters with 3-4 ice cubes and stir until well chilled, about 30-45 seconds. Strain into chilled rocks glass with a couple fresh ice cubes and garnish with a pineapple wedge, cocktail cherry and a couple pineapple leaves skewered on a cocktail pick.
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Pineapple Syrup
1 Cup Brown Sugar
1 Cup Pineapple Juice
½ Pineapple, peeled, cored and cut into 1/2” thick wedges
2 oz Cal & Gary's Premium Spiced Rum
½ oz Pineapple Syrup
2-3 Dashes Angostura Bitters
Approx 1 Cup Ice Cubes
Grilled Pineapple Wedges, Cocktail Cherries, Pineapple Leaves, for garnish