Muddle four of the pineapple chunks, one of the orange wedges, and one of the lemon wedges with the Cherry Heering in a cocktail shaker. Add the gin and ice, shake, and strain into an ice-filled rocks glass. Garnish with the remaining pineapple chunk, orange wedge, and lemon wedge.

• 1 ½ oz bourbon
• ¾ oz ruby port
• ¾ oz lemon juice
• ¼ oz simple syrup
• 2 orange wedges
• 2 lemon wedges
• 4 1-inch square pineapple chunks
• fizz water

Muddle the pineapple chunks, one of the orange wedges, and one of the lemon wedges with the simple syrup and lemon juice in a cocktail shaker. Add the whiskey and port, and ice. Shake and strain into an ice-filled highball glass. Top with fizz water and garnish with the remaining orange and lemon wedges.

• 4 oz ruby port
• ½ oz orange curaçao
• 5 1-inch square pineapple chunks
• 2 orange wedges
• 2 lemon wedges

In a cocktail shaker, muddle 4 of the pineapple chunks, 1 orange wedge, and 1 lemon wedge with the curaçao. Add the port and ice, shake, and strain into a rocks glass filled with crushed ice. Garnish with the remaining orange wedge, lemon wedge, and pineapple chunk.

• 2 oz whiskey of choice
• ¾ oz orange curaçao
• 4 1-inch square pineapple chunks
• 2 orange slices
• 2 lemon wedges

Muddle 3 of the pineapple chunks, 1 orange slice, and 1 lemon wedge with the orange curaçao in a cocktail shaker. Add the whiskey and ice, shake, and strain into a rocks glass filled with crushed ice. Garnish with the remaining orange slice, lemon wedge, and pineapple chunk.