Spread shredded coconut in a thin layer on a baking sheet and toast in a 350°F (175°C) oven for 5–8 minutes, stirring once, until golden brown and fragrant. Remove and cool. Alternatively, toast in a dry skillet over medium heat, stirring constantly, until golden. Let cool.

Prepare rim

Pour the cooled toasted coconut onto a small plate. Wet the rim of a chilled hurricane or highball glass by brushing the 0.5 oz simple syrup (or a little high-proof rum) around the rim. Dip the wet rim into the toasted coconut, pressing gently so the coconut adheres evenly. Set the glass aside.

Cocktail

Fill a cocktail shaker with the ice (if you prefer a slightly slushy Painkiller, use crushed ice).

Add 2 oz aged Cruzán rum, 4 oz pineapple juice, 1 oz creme of coconut, and 1 oz fresh orange juice to the shaker.

Shake vigorously for 10–15 seconds until the outside of the shaker is well-chilled and the ingredients are combined and slightly frothy from the creme of coconut.

Strain (or dump, if you prefer a more casual presentation) the contents into the prepared glass over fresh ice (cubed or crushed, according to preference).

Garnish with a pineapple wedge and an orange wheel on the rim or skewer them together and rest on the glass. Finish with a light grating of fresh nutmeg (about 1/4–1/2 tsp) over the top, if using.

Serve immediately with a straw and enjoy.