Roasted Tomato Pesto Grilled Cheese (Printable)

Gourmet grilled cheese with slow-roasted tomatoes, basil pesto, and layers of mozzarella and cheddar 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 - Handful of baby spinach or arugula leaves, optional

# How To Make It:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper.
02 - Arrange tomato slices on the 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. Remove from oven and let cool slightly.
03 - Spread softened 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 2 slices mozzarella, roasted tomatoes, and 2 slices cheddar on each. Top with remaining bread slices, buttered side up. Add spinach or arugula between cheese layers if desired.
05 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is completely melted.
06 - Remove sandwiches from heat, slice in half diagonally, and serve immediately.

# Expert Tips:

01 -
  • The roasted tomatoes turn sweet and jammy, adding a depth you cannot get from fresh slices.
  • Every bite has contrast: crispy bread, creamy cheese, and that bright herby pesto.
  • It feels fancy enough for guests but easy enough for a rainy Tuesday lunch.
  • You can prep the tomatoes ahead and assemble sandwiches in minutes.
02 -
  • Do not rush the roasting, those tomatoes need time to caramelize and concentrate their flavor.
  • If your heat is too high, the bread will burn before the cheese melts, so keep it medium low and be patient.
  • Spread the pesto all the way to the edges so every bite has that herby brightness.
03 -
  • Use a cast iron skillet if you have one, it holds heat evenly and gives the bread an extra crispy crust.
  • Press the sandwich gently with a spatula while it cooks to help the cheese melt faster without cranking up the heat.
  • Let the roasted tomatoes cool slightly before layering so they do not make the bread soggy.
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