Cook the penne pasta according to package instructions until al dente. Drain and set aside, reserving 1/2 cup of the pasta water.
In a large skillet, heat the olive oil over medium heat. Add the sliced kielbasa and cook until browned, about 5-7 minutes.
Stir in the minced garlic and cook for an additional 1-2 minutes until fragrant.
Add the fresh spinach and cherry tomatoes to the skillet. Cook until the spinach is wilted and the tomatoes are softened, about 3-4 minutes.
Toss the cooked pasta into the skillet with the kielbasa mixture. Add the Italian seasoning, salt, and pepper. If the pasta seems dry, add a little reserved pasta water to reach the desired consistency.
Remove from heat and stir in the grated Parmesan cheese until well combined.
Serve hot, garnished with additional Parmesan if desired.