Combine sugar, water, and vanilla extract in a medium saucepan and heat over medium heat, stirring until sugar dissolves.

Bring the mixture to a boil, then reduce heat to medium-low and simmer for 5 minutes.

Remove from heat and let cool slightly.

Add pitted cherries to the saucepan and let them steep in the sugar mixture for 10-15 minutes.

Strain cherries from the sugar mixture using a slotted spoon and place them in a clean glass jar.

Pour bourbon whiskey over the cherries, ensuring they are completely covered.

Seal the jar and store in a cool, dark place for at least 2 weeks, shaking the jar every few days.

After 2 weeks, the bourbon soaked cherries are ready to use and can be stored in the refrigerator for up to 6 months.