Combine the chopped fresh pineapple, granulated sugar, and water in a small saucepan over medium heat. Stir until sugar dissolves and mixture comes to a gentle simmer.

Simmer for 8–10 minutes, crushing the pineapple gently with the back of a spoon to release juices and flavor. Do not boil vigorously; aim for a steady gentle simmer to extract flavor.

Remove from heat, stir in lime zest, and let the syrup steep and cool for 20–25 minutes to deepen flavor.

Strain the syrup through a fine mesh sieve or cheesecloth into a clean container, pressing on solids to extract as much liquid as possible. Discard solids or reserve for another use. Chill syrup until ready to use. Yield: ~1 cup.

Cocktail Assembly

If you want a sugared or coconut rim: rub a lime wedge around the rim of a rocks or Collins glass, then dip rim into coarse sugar or toasted coconut on a small plate. Set glass aside.

Fill a cocktail shaker halfway with ice (about 1 cup). Add dark rum, pineapple vodka, 0.75 oz chilled pineapple simple syrup, fresh lime juice, pineapple juice, and 2 dashes Angostura bitters.

Shake vigorously for 10–15 seconds until the shaker is cold to the touch and the mixture is well chilled and slightly diluted.

Fill the prepared glass with fresh ice. Strain the shaken cocktail into the glass (use a fine strainer if you prefer a clearer drink).

Garnish with a pineapple wedge, a lime wheel, and a sprig of fresh mint. Optionally slap the mint once between your hands before garnishing to release aroma.

Serve immediately with a short stirring straw or stirrer so drinkers can incorporate garnish oils if desired.