Preheat your oven to 400°F (200°C). In a mixing bowl, toss the halved cherry tomatoes with olive oil, minced garlic, dried oregano, dried basil, crushed red pepper flakes, salt, and pepper until everything is evenly coated.
Transfer the tomatoes to your oven-safe skillet, spreading them out evenly. Place the block of feta cheese right in the center of the skillet, nestling it among the tomatoes. Roast in the preheated oven for 30 minutes until the tomatoes are bursting and the feta is golden and soft.
While the tomatoes and feta roast, bring a medium pot of salted water to a boil. Add the orzo and cook according to the package instructions, usually around 7-9 minutes, until al dente. Drain the orzo and set aside.
Remove the skillet from the oven. Using a fork or spoon, mash the roasted feta and tomatoes together to create a creamy sauce. Add the cooked orzo and chopped spinach to the skillet, stirring gently until the spinach wilts and everything is well combined. Taste and adjust seasoning with salt and pepper.
Sprinkle fresh basil leaves over the skillet before serving. This dish is best enjoyed warm and fresh from the oven, paired with a crisp salad or some crusty bread to soak up the sauce.