Assemble, tomatoes, basil (roll from one end to the other), and mozzarella balls on medium-sized toothpicks. Drizzle with olive oil and sprinkle with salt and pepper.
To make balsamic glaze, add one cup of balsamic vinegar to a sauce pan over medium heat. Once it comes to a boil, set on simmer for about 10-15 minutes until it reduces to a syrup consistency. You can check by dipping a spoon in the balsamic and if it covers the back of it, it's done.
As it cools, it will thicken a bit more then drizzle on top of caprese salad skewers, or serve drizzle on the side as a dipping sauce.