Preheat the oven to 400°F / 200°C.
Add the cherry tomatoes to a baking dish. Toss them with olive oil, garlic, Italian seasoning, salt, black pepper, and red pepper flakes.
Roast the tomatoes for 20–25 minutes, until softened, juicy, and lightly caramelized.
While the tomatoes roast, heat one tablespoon of olive oil in a large skillet over medium heat. Add the shallot and cook for 2–3 minutes.
Stir in the dry orzo and toast it for about one minute.
Pour in the vegetable broth. Bring to a gentle simmer and cook for 10–12 minutes, stirring regularly, until the orzo is tender and most of the broth has been absorbed.
Reduce the heat to low. Stir in the heavy cream, Parmesan, spinach, and lemon juice. Cook until the spinach wilts and the sauce becomes creamy.
Add the roasted tomatoes and their juices to the orzo. Stir gently and season with additional salt and pepper as needed.
Add the feta, Greek yogurt, olive oil, lemon zest, and lemon juice to a food processor. Blend until smooth and creamy.
Spoon the creamy tomato orzo into serving bowls. Top each serving with whipped feta, fresh basil, Parmesan, and cracked black pepper.