Combine all ingredients in a shaker and dry shake without ice for 15 seconds. Add ice to the shaker & shake again for 15 seconds. Strain over a rocks glass with ice. Garnish with fresh rosemary and a cherry.
Create the apple simple syrup by combining 1 cup of sugar with 1 cup of water in a small saucepan. Bring mixture to a boil to dissolve the sugar. Add in 1 chopped apple (including the core) and let simmer for 5 minutes. Remove from heat and allow to cool completely. Strain to remove the solids and store in an airtight container in the fridge up to 1 week.