Preheat your oven to 400°F (200°C). Spread the halved cherry tomatoes on a baking sheet, drizzle with 1 tablespoon of olive oil, and sprinkle with salt and pepper. Roast in the oven for 20-25 minutes until they are soft and slightly caramelized.
While the tomatoes are roasting, cook the pasta according to package instructions in a large pot of salted boiling water. Drain and set aside, reserving 1/2 cup of the pasta water.
In a food processor, combine the roasted cherry tomatoes, basil leaves, Parmesan cheese, garlic, remaining olive oil, and pine nuts (if using). Blend until smooth, adding reserved pasta water a little at a time to reach your desired consistency.
In a large mixing bowl, combine the cooked pasta and the pesto sauce. Toss until the pasta is evenly coated.
Serve immediately, garnished with additional Parmesan cheese and fresh basil if desired.