Bring a large pot of generously salted water to a boil in the cream Dutch oven. Add the tortellini and cook according to the package directions, about 7 to 9 minutes, until just al dente: it should still offer slight resistance at the center.
Drain the tortellini in a colander and rinse under cold running water for about 30 seconds to stop the cooking and cool it quickly.
Transfer the tortellini to a white ceramic mixing bowl, pour over 1/2 cup of the Italian dressing, and toss gently until every piece is coated and glossy.
Cover the bowl with plastic wrap and refrigerate for at least 2 hours, or overnight, until the tortellini feels firm and has taken on the color of the dressing.
While the tortellini chills, fold each slice of salami into quarters so it sits as a small fan rather than lying flat.
Arrange the mozzarella pearls, olives, cherry tomatoes, basil leaves and folded salami in small bowls on a pale wood board so you can see every color before you start threading.
Take one 6-inch wooden skewer and thread, in this order: one olive, one cherry tomato, one folded salami, one mozzarella pearl, one basil leaf, one marinated tortellini. Push each piece down gently so the skewer feels snug, not crowded.
Repeat the same six-ingredient sequence once more on the same skewer, so it reads as two matching layers from pointed tip to handle, then set it on a large white ceramic platter.
Thread the remaining skewers the same way, laying each one on the platter as you finish it, until all the ingredients are used.
Cover the platter tightly with plastic wrap and refrigerate overnight, or for at least 4 hours, so the flavors settle and everything chills through evenly.
About 20 minutes before your guests arrive, take the platter out of the refrigerator and let the skewers lose their chill at room temperature.
Drizzle the remaining Italian dressing over the skewers just before serving, so the top layer looks freshly dressed rather than soaked, and set the platter out.
Good to Know
Keep the basil out until the morning you serve if you are building more than a day ahead: it holds its color far better than if it sits in the dressing overnight.