To make cinnamon syrup: in a small or medium saucepan, combine one cup of water, 4-5 broken up cinnamon sticks and bring to a light simmer. Add in one cup of sugar, and gently stir to dissolve the sugar. Maintain a very light simmer for 5-10 minutes, then remove from the heat and allow the syrup to cool. Once cooled, strain the syrup through a fine mesh strainer to remove the cinnamon sticks and store the syrup in a glass jar in the refrigerator up to 2 weeks.
To make grilled pineapple juice: slice one pineapple into 1/2 inch thick pieces. Oil grates of grill so that pineapple doesn't stick. Char pineapple slices and let cool. Reserve one slice for garnish, and juice remaining slices.
Combine all ingredients into a cocktail shaker and shake with ice. Strain the cocktail into a rocks glass over ice. Garnish with a grilled pineapple wedge.
Elliott Clark, also known as the Apartment Bartender, is a well-respected tastemaker, cocktail creator, spirits writer, and photographer in the spirits industry. What started out as a hobby for making cocktails at home has developed into a full-blown career that takes Elliott all over the world mixing drinks for some of the world’s most notable brands, and making the world of spirits more accessible to the at-home cocktail enthusiast.