Bring a medium pot of salted water to a boil. Add the penne pasta and cook according to package instructions until al dente. Drain the pasta in a colander and rinse with cold water to cool it down.

In a large mixing bowl, combine the halved cherry tomatoes, diced cucumber, diced bell pepper, finely chopped red onion, and Kalamata olives.

Once the pasta has cooled, add it to the bowl with the vegetables.

In a separate bowl, whisk together the extra virgin olive oil, red wine vinegar, dried oregano, salt, and pepper until well combined.

Pour the vinaigrette over the pasta salad and toss gently to coat all the ingredients evenly.

Add the crumbled feta cheese to the salad and toss again carefully, ensuring not to break the cheese too much.

Garnish with fresh parsley if desired, and serve immediately or refrigerate for at least 30 minutes to allow the flavors to meld.