Roasted Tomato Pesto Grilled Cheese (Printable)

Gourmet grilled cheese featuring slow-roasted tomatoes, basil pesto, and layers of melted cheese on rustic bread.

# What You'll Need:

→ 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

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 - Optional: handful of baby spinach or arugula leaves

# Directions:

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

# Expert Tips:

01 -
  • The roasted tomatoes become candy-sweet and umami-rich, completely transforming the ordinary grilled cheese into something restaurant-worthy
  • This recipe strikes that perfect balance between comfort food nostalgia and gourmet ingredients that make you feel like youve treated yourself
02 -
  • Low and slow heat is essential here, as high heat will burn the bread before the cheese has time to melt
  • The tomatoes need to cool slightly before assembling, or they will make your bread soggy
03 -
  • Use a cast iron skillet if you have one, as it distributes heat evenly and creates the best crust
  • Add a pinch of red pepper flakes to the pesto for subtle heat that cuts through the cheese
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