Roasted Tomato Pesto Grilled Cheese (Printable Version)

Slow-roasted tomatoes, basil pesto, and melted cheese on rustic bread for an elevated comfort meal.

# What You 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 - Handful of baby spinach or arugula leaves, optional

# Steps:

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

# Expert Advice:

01 -
  • The roasted tomatoes become these incredible umami bombs that put regular grilled cheese to shame
  • That pesto and sharp cheddar combination hits corners of your palate you forgot existed
02 -
  • Medium-low heat is non-negotiable because the cheese needs time to melt before the bread burns
  • Dont skip the parchment paper when roasting tomatoes or you will spend forever scrubbing your baking sheet
03 -
  • Roast extra tomatoes and keep them in your fridge they elevate everything from pasta to eggs all week long
  • Let the assembled sandwiches sit for 5 minutes before cooking to let the bread absorb some of the pesto flavor
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