Chill a Collins glass or large rocks glass by filling it with ice water while you assemble ingredients. After a minute, discard the ice water and add about 1 cup of crushed ice to the glass (reserve one large cube if using).

Build the base

In a cocktail shaker (no need to dry shake), add 2 oz light rum, 3 oz fresh pineapple juice, 1 oz fresh orange juice, 0.5 oz fresh lime juice, 0.25 oz simple syrup and 2 dashes Angostura bitters. Add a handful of ice to the shaker (about 4-6 small cubes).

Shake

Shake vigorously for 12-15 seconds until well chilled and slightly diluted (shaker becomes cold to the touch).

Strain

Double-strain the shaken mixture into the prepared glass over the crushed ice, leaving room on top for the grenadine and the dark rum float.

Add grenadine for 'sunset' effect

Slowly pour 0.5 oz grenadine down the inside edge of the glass or over the back of a spoon so it sinks toward the bottom and creates a layered red-to-golden gradient that resembles a Hawaiian sunset.

Float dark rum

Gently pour 0.25 oz dark rum over the back of a spoon at the surface of the drink to create a thin, dark float on top. This adds aroma and visual contrast.

Final touches

If you removed the large ice cube earlier, add it now so the drink has a mix of crushed ice and a large cube (this slows dilution). Garnish with a pineapple wedge and a maraschino cherry on a pick; optionally add an orange wheel on the rim.

Serve

Serve immediately with a straw placed off to the side so the guest can experience the layered colors before stirring. Recommend stirring gently before drinking to combine flavors.