Bring a large pot of lightly salted water to a boil. Cook the tortellini according to the package directions, usually about 5–7 minutes, until tender. Drain and rinse under cold water to stop the cooking process.
Transfer the tortellini to a colander and drain thoroughly. Pat them gently with paper towels to remove excess moisture so they are easier to thread onto the skewers.
Wash and dry the tomatoes, drain the mozzarella and olives, and tear the basil into smaller pieces if the leaves are large.
Thread the ingredients onto each skewer, alternating tortellini, tomato, mozzarella, olive, and basil. Repeat the pattern until each skewer is filled but still easy to hold.
Arrange the finished skewers on a large serving platter. Sprinkle evenly with salt and freshly ground black pepper.
Drizzle the skewers lightly with extra-virgin olive oil, followed by balsamic glaze. Add a few extra basil leaves for a fresh finish.
Refrigerate the assembled skewers for at least 15–20 minutes before serving, or cover and refrigerate for up to 24 hours. Add the oil and balsamic glaze just before serving for the freshest presentation.
