Combine 1/2 cup granulated sugar and 1/2 cup water in a small saucepan. Heat gently over medium heat, stirring until sugar dissolves. Remove from heat, stir in 1 tsp pure vanilla extract. Let cool, transfer to a jar, refrigerate. Yields ~12 fl oz; use 1/2 oz for the cocktail.

Make cinnamon syrup

In a small saucepan combine 1/4 cup sugar, 1/4 cup water and 1 tsp ground cinnamon (or 2 small cinnamon sticks). Bring to a simmer for 3–4 minutes, stirring to dissolve. If using sticks, simmer 6–8 minutes for more flavor. Cool, strain if using sticks or ground cinnamon. Store refrigerated. Yields ~6 fl oz; use 1/4 oz for the cocktail.

Build & Shake

Fill a cocktail shaker with ice to chill.

Add 2 oz Havana Especial rum, 1 oz cranberry juice, 1.25 oz fresh pineapple juice, 0.5 oz fresh lemon juice, 0.5 oz vanilla syrup and 0.25 oz cinnamon syrup to the shaker.

Dry shake (no ice) for 8–10 seconds if you want a slightly frothy texture, then add ice and shake vigorously for 10–12 seconds until well chilled.

Prepare a tiki glass or double old-fashioned glass by filling it with crushed or cracked ice (~1 cup).

Double-strain the shaken cocktail over the crushed ice using a Hawthorne and fine strainer to remove small ice shards and any pulp.

Garnish & Finish

Thread 3 cranberries onto a small cocktail pick and rest on the rim or lay across the ice.

Place a dried pineapple wheel or fresh pineapple wedge on the rim or spike it into the ice.

Add a cinnamon stick upright into the drink for aroma. Optionally express the lemon peel over the drink (twist and run the peel around the glass) and quickly flame it with a lighter for a brighter aromatic finish; discard peel into the drink or drop on top of the ice.

Serve immediately with a short straw. Encourage sipping to enjoy the layered notes of cinnamon, vanilla, tart cranberry and tropical pineapple alongside the Havana Especial rum.