In a bowl, mix 2 cups of flour and 1/2 teaspoon of salt, then set aside. In a separate bowl, cream 1 cup of room-temperature unsalted butter with 1/2 cup powdered sugar until light and fluffy. Mix in 1/2 tablespoon vanilla extract until well combined.

Gradually add the flour and salt mixture to the butter-sugar mixture, mixing until the dough forms larger clumps. Be careful not to overmix.

Gently fold in 3/4 cup chopped and well-drained maraschino cherries and 2/3 cup chocolate chips until evenly distributed throughout the dough.

Shape the dough into a log about 2 inches thick, pressing it together well. Wrap in plastic wrap and chill in the refrigerator for at least 1-2 hours, or until firm.

Preheat the oven to 325°F (160°C) and line a baking sheet with parchment paper.

Slice the chilled dough log into 1/4 to 1/3 inch thick rounds. Place the slices on the prepared baking sheet, leaving about an inch of space between each.

Bake in the preheated oven for 10 to 15 minutes, or until the tops are lightly golden. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.