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Preheat oven to 375°F. Arrange tomatoes on a large rimmed baking sheet in a single layer. Drizzle with 2 tablespoons of the oil and season with some of the salt and pepper; set aside. Arrange eggplant on a second large rimmed baking sheet, drizzle with 2 tablespoons of the remaining oil and season with the remaining salt and pepper. Roast tomatoes and eggplant, rotating trays halfway through, until tomatoes are softened and beginning to char and eggplant is browned and softened, 30 to 40 minutes; set aside.
In a large, deep skillet, heat remaining 1/4 cup oil over medium heat. Add garlic and cook, stirring frequently, until the garlic starts to brown, about 1 minute. Add wine and simmer until reduced by about half, 6 to 8 minutes.
Meanwhile, bring a large pot of salted water to a boil. Add pasta and cook according to the package directions.
Add tomatoes, eggplant and olives to the garlic-wine mixture in skillet. As soon as the pasta is cooked, drain and add to skillet along with 1 or 2 tablespoons of the starchy pasta cooking water. Toss to combine well. Add ricotta salata, Pecorino Romano and basil and toss gently to combine. Serve immediately.