Place the broth into a heavy-bottomed large saucepan over high heat. Once the broth reaches a boil, stir in the orzo. Reduce heat to low and cook, stirring often, until the orzo is al dente, about 7 minutes. Drain the orzo and place it in a large bowl, tossing it with the remaining 2 teaspoons olive oil. Set aside to cool.
Meanwhile, while the orzo is cooling, pour ½ cup of the extra virgin olive oil in a large sauté pan over medium-low heat. Add the 5 basil leaves (left whole), shallots, bell peppers, 6 ounces of the cherry tomatoes, and garlic. Season with 1 teaspoon salt, and cook, stirring often, until the tomatoes blister and the peppers soften, 20 to 25 minutes.
Once the vegetables are done, use a slotted spoon to transfer them into the same bowl as the orzo, draining as much oil through the slots as possible. Transfer the infused oil to a bowl and let it cool about 10 minutes.
While the oil is cooling, cut the remaining tomatoes in half and add them to the bowl of orzo and peppers, along with the cucumbers.
To the oil, add the vinegar, lemon juice, lemon zest, maple syrup, remaining ½ teaspoon salt, pepper, dried oregano, dried parsley, and red pepper flakes.
Before serving, I like to chill the orzo/pepper mixture and dressing separately for about an hour, but this salad can also be enjoyed at room temperature.
To serve, fill a large serving bowl with the arugula and top with the orzo/pepper mixture and dressing. Toss to combine, ensuring everything is well incorporated. Finish with vegan feta (if using) and serve alongside a couple wedges of fresh lemon and enjoy!