Roasted Tomato Pesto Grilled Cheese (Printable Version)

Golden sourdough layered with slow-roasted tomatoes, basil pesto, and melted mozzarella and cheddar for a comforting vegetarian lunch.

# List of Ingredients:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4-inch thick
02 - 1 tablespoon olive oil
03 - 1/4 teaspoon sea salt
04 - 1/4 teaspoon freshly ground black pepper
05 - 1/4 teaspoon dried oregano

→ Sandwich Assembly

06 - 4 slices rustic sourdough or country bread
07 - 2 tablespoons unsalted butter, softened
08 - 2 tablespoons basil pesto
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Handful baby spinach or arugula leaves (optional)

# How-To Steps:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the prepared sheet, drizzle with olive oil, and season with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still hold their shape. Allow to cool slightly.
02 - Spread softened butter evenly on one side of each bread slice. Place 2 slices butter-side down on a clean work surface.
03 - Spread 1 tablespoon of pesto on each unbuttered side. Layer 2 slices of mozzarella, roasted tomatoes, 2 slices of cheddar, and spinach or arugula if using. Top with remaining bread slices, buttered side facing up.
04 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook for 4–5 minutes per side, pressing gently with a spatula, until golden brown and cheese is completely melted.
05 - Transfer sandwiches to a cutting board, slice diagonally in half, and serve immediately while hot.

# Expert Suggestions:

01 -
  • The roasted tomatoes become candy-sweet and savory, adding depth you can't get from fresh tomatoes
  • This sandwich hits that perfect balance of crispy bread, tangy pesto, and three cheeses melting together
02 -
  • Low and slow is the secret to the tomatoes, high heat makes them watery instead of sweet
  • Medium-low heat for grilling lets the cheese melt before the bread burns
03 -
  • If your roasted tomatoes release too much liquid, pat them gently with paper towels before assembling
  • A cast iron skillet creates the most evenly golden, crispy crust
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