Bring a large pot of salted water to a rolling boil. Add the penne pasta and cook according to package directions, about 10-12 minutes, until al dente. Drain the pasta but do not rinse.

In a medium-sized bowl, combine halved cherry or grape tomatoes, olive oil, red wine vinegar, minced garlic, kosher salt, and freshly ground black pepper. Whisk to emulsify and set aside for 10-15 minutes.

In a large mixing bowl, combine chopped cucumbers, halved black olives, diced red onion, and the cooked penne pasta. Gently stir everything together.

Pour the prepared tomato dressing over the pasta mixture and toss gently to coat evenly.

Add fresh basil and parsley over the salad. Toss again, adjusting seasoning as needed.

Serve immediately or chill in the refrigerator for at least 30 minutes for enhanced flavor.