While waiting for the pasta water to boil, whisk together the olive oil, red wine vinegar, lemon juice, honey, freshly pressed garlic, oregano, salt, pepper, and red pepper flakes in a bowl. The acidity and oil will emulsify slightly as you whisk, creating a cohesive dressing that will coat the pasta evenly. I find that letting the vinaigrette sit for a few minutes allows the garlic and herbs to infuse their flavors more deeply into the oil and vinegar base.
Bring a large pot of salted water to a boil and cook the pasta according to package directions until al dente. While the pasta cooks, prepare your vegetables: peel and slice the cucumber into 1/2-inch half-moons, halve the cherry tomatoes, thinly slice the red onion, and chop the fresh parsley. Having all your vegetables prepped ensures the salad comes together quickly once the pasta is ready.
Drain the cooked pasta and rinse briefly with cold water for 20-30 seconds to stop the cooking process and remove excess starch—this prevents the pasta from becoming gummy. Transfer the still-slightly-warm pasta to a large mixing bowl and immediately pour the vinaigrette from Step 1 over it, tossing well to coat. The warm pasta will absorb the dressing more effectively, creating better flavor throughout the salad.
Add the prepared cucumber, tomatoes, sliced kalamata olives, crumbled feta, sliced red onion, and chopped parsley from Step 2 to the dressed pasta. Toss everything together gently but thoroughly to distribute the dressing and combine all flavors evenly. Taste and adjust seasonings if needed—the salad is ready to serve immediately, or you can refrigerate it until serving time.