Add balsamic vinegar to a small saucepan over high heat then bring to a boil. Turn heat down to medium then simmer until vinegar is the consistency of thin maple syrup, about 20 minutes. Pour balsamic reduction into a small bowl then set aside to cool. Can be made then refrigerated up to 5 days ahead of time.

Thread a cheese ball onto a toothpick, followed by a basil leaf - fold in half or into quarters if large. Finish with a cherry tomato then place onto a serving platter. Repeat with remaining ingredients. Just before serving, sprinkle skewers with salt and pepper then drizzle with cooled balsamic reduction. Serve immediately.