Preheat oven to 400°F. Spread the halved cherry tomatoes on a baking sheet. Drizzle with 2 tbsp olive oil and season with garlic, oregano, red pepper flakes, salt and pepper.
Roast for 25-30 minutes, until tomatoes are softened and starting to caramelize.
Cook the penne pasta according to package instructions. Drain and set aside.
In a large skillet, heat the remaining 1 tbsp olive oil over medium heat. Add the roasted tomatoes and any juices from the baking sheet.
Pour in the heavy cream and parmesan cheese. Stir to combine and let simmer for 2-3 minutes until slightly thickened.
Add the cooked penne and baby spinach. Toss to coat the pasta in the creamy tomato sauce.
Remove from heat and stir in the chopped fresh basil.
Serve immediately, garnished with extra parmesan if desired.
