These Italian-style grilled cheese sandwiches, recipe courtesy of Jennifer Segal at Once Upon a Chef,  are zhushed up with sun-dried tomato pesto and taste like hot, crispy pizza panini. They are the perfect guilty pleasure and the perfect addition to any picnic basket.

Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

Servings: 4


For the Sun-Dried Tomato Pesto (makes 1-1/2 cups)

    • 1 (8.5-ounce) jar sun-dried tomatoes packed in olive oil
    • 2 cloves garlic
    • ½ teaspoon salt
    • ¼ teaspoon crushed red pepper flakes
    • ½ teaspoon sugar
    • 1 cup packed fresh basil leaves
    • ¼ cup + 2 tablespoons pine nuts
    • ⅓ cup freshly grated Parmigiano-Reggiano
    • 2 tablespoons water

For the Grilled Cheese Sandwiches

    • 8 slices Italian bread
    • 4 tablespoons softened butter
    • 8 oz fontina or Gruyere (or any good melting cheese), sliced or grated
    • ½ cup sun-dried tomato pesto


For the Sun-Dried Tomato Pesto

  • In the bowl of a food processor fitted with the steel blade, combine the sun-dried tomatoes with the oil, garlic, salt, red pepper flakes, sugar, basil, pine nuts, Parmigiano-Reggiano and 2 tablespoons of water. Pulse, scraping down the sides as necessary, until the mixture is finely puréed.

For the Grilled Cheese Sandwiches

  • Spread one side of each slice of bread with butter, then flip over and spread the pesto evenly over the other side of each slice. Heat a large nonstick or cast iron pan over medium heat. Place 4 slices of bread, butter side down, in the pan. Divide the cheese evenly over the bread, then top the sandwiches with the remaining bread. Cook until the first side is golden brown, a few minutes. Carefully flip the sandwiches and cook until the cheese is fully melted and the bread is golden brown, a few minutes more. Let cool slightly, then slice the sandwiches in half and serve.

Note: You’ll have plenty of leftover sun-dried tomato pesto. It keeps well in the refrigerator for up to 4 days and can be frozen for up to 2 months. You can also try tossing the pesto with pasta; just keep in mind that the pesto is thick so you’ll need to thin it with some of the pasta cooking water and a little olive oil.

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