In a blender or food processor, combine 1 cup fresh basil leaves, 1/3 cup grated Parmesan cheese, 1/4 cup pine nuts, 2 cloves garlic, 1/2 teaspoon salt, and 1/4 teaspoon black pepper. Pulse until finely chopped.
With the blender or food processor running, slowly drizzle in 1/3 cup extra virgin olive oil until the mixture forms a smooth pesto. Set aside.
In a large pot, add 12 ounces dried penne pasta and 4 cups water. Bring to a boil over high heat.
Reduce heat to medium and cook the pasta, stirring occasionally, until al dente and most of the water has been absorbed, about 10-12 minutes.
Remove the pot from heat. Stir in the prepared pesto and 1 cup halved cherry tomatoes until the pasta is evenly coated.
Divide the pasta among serving plates. Garnish each plate with fresh basil leaves and 2 tablespoons grated Parmesan cheese.
Serve immediately.