Add the broccoli florets and cherry tomatoes to a rimmed sheet tray. Drizzle with 1/4 cup olive oil and season with salt and pepper. Toss to coat completely. Roast for 20 to 25 minutes, until the broccoli is tender and lightly golden brown.
Toss with arugula and crumbled feta cheese. Drizzle with remaining 2 tablespoons olive oil. Season with salt and pepper and toss. Serve immediately.