Grill the pineapple wedges to achieve grill marks. (The natural sugars in the pineapple will caramelize.) 2. In a glass, muddle 2 wedges of the grilled pineapple with the vanilla bean and simple syrup. Pour the rum and lime juice into a shaker. Add ice and shake. Double-strain into a cocktail glass.
Dust the remaining pineapple wedge with black pepper and use to garnish the drink. Serve immediately.