Cook pasta according to package directions. Drain and rinse pasta under cold water to stop cooking.
Meanwhile, whisk together the vinegar, olive oil and smashed garlic in a medium bowl. Season with salt and pepper, to taste, and toss with the tomatoes, olives, cheese and cooked pasta. Skewer everything, alternating as desired. Place marinara sauce or pesto in sealed containers. Pack in a lunch sack with an ice pack and send off to school.
TIP: For young children, we recommend cutting the pointy end off the skewer with sharp kitchen scissors/shears.