How to Make It
Fill a julep cup with crushed ice. Fill a cocktail shaker with large ice cubes; add Madeira, rum, simple syrup, orange peel strips, lemon peel strip, and 5 blackberries. Cover and shake vigorously until well chilled, about 10 seconds. Strain into prepared cup; top with crushed ice and remaining 5 blackberries. Garnish with pineapple wedge. Serve with a straw.