Roasted Tomato Pesto Grilled Cheese (Printable)

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

# Ingredient list:

→ 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 - Roasted tomatoes from preparation
12 - 1 handful baby spinach or arugula leaves, optional

# Step-by-Step Guide:

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, 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. Let 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 each unbuttered side. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Cover with remaining bread slices, buttered side up.
05 - 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.
06 - Slice sandwiches in half and serve immediately.

# Expert Advice:

01 -
  • The roasted tomatoes become sweet and intense, like a concentrated burst of summer that perfectly cuts through rich melted cheese
  • This is the kind of grilled cheese that makes you pause and really savor each bite instead of just inhaling it like a regular sandwich
02 -
  • Do not rush the tomato roasting step because those 60 minutes are what transform ordinary tomatoes into something extraordinary
  • Medium-low heat is crucial for the grilled cheese step because high heat will burn the bread before the cheese has time to melt completely
03 -
  • Use a cast iron skillet if you have one because it creates the most even, golden crust
  • Letting the roasted tomatoes cool slightly before assembling prevents the bread from getting soggy
Return