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Preheat oven to 400°F. Bring a kettle of water to a boil.
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Place 3/4 cup couscous in a small bowl with a pinch of salt and a drizzle of olive oil. Pour 2/3 cup boiling water over the couscous, stirring to combine. Cover the bowl with plastic wrap and set aside.
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Bring 2 cups of water to a boil in a medium saucepan. Add a pinch of salt and 1 cup of Israeli couscous. Simmer until al dente (soft on the outside, some bite left on the inside, about 16 - 18 minutes). Drain the Israel couscous then rinse under cold running water. Let dry then add to a large bowl. Fluff regular couscous with a fork then add to the same bowl.
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Spread yellow cherry tomatoes out on a baking sheet and drizzle with a little olive oil. Sprinkle with kosher salt and black pepper then roast for 12 -13 minutes. The tomatoes will start to collapse and turn golden brown. Set aside to cool.
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To the bowl with the couscous, add roasted yellow tomatoes, orange tomato wedges, halved red cherry tomatoes, sliced sun-dried tomatoes, oregano, tarragon and mint.
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Prepare the vinaigrette by placing minced sun-dried tomatoes, both vinegars, garlic and olive oil in a mason jar. Season with a pinch of kosher salt and several turns of black pepper. Lid the jar and shake until well-combined.
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Spoon some of the vinaigrette over the salad then gently toss to combine. I didn't use all of the vinaigrette. Season to taste with additional kosher salt and freshly ground black pepper.