- Seven 1/2-inch-thick pineapple wheels—2 unpeeled and 5 peeled
- About 1/4 cup pineapple juice
- 6 ounces Japanese whisky
- 6 ounces Islay Scotch
- 6 ounces dark rum, preferably Gosling's Black Seal
- 4 ounces orange Curaçao
- 4 ounces fresh orange juice
- 4 ounces fresh lemon juice
- 4 ounces grenadine, preferably homemade
- 8 small hollowed pineapples, for serving (optional)
- 8 cocktail umbrellas, for garnish
Preheat a grill pan over high heat. Grill all of the pineapple wheels until they are charred, about 5 minutes per side. Cut each unpeeled pineapple wheel into 4 wedges and reserve them for garnish.
Cut the peeled pineapple wheels into small pieces. In a blender, puree the peeled pieces, adding up to 1/4 cup pineapple juice to help blend. Strain the puree into a measuring cup, transfer 8 ounces of the grilled pineapple juice to a pitcher (reserve the rest for another use), then stir in the whisky, Scotch, rum, Curaçao, orange juice, lemon juice and grenadine.
Pour half of the mixture into the blender, add 2 cups of ice and blend until slushy. Pour into 8 chilled tiki mugs or hollowed pineapples. Garnish each drink with a grilled pineapple wedge and a cocktail umbrella. Repeat for the remaining servings.