Roasted Tomato Pesto Grilled Cheese (Printable)

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

# 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, homemade or store-bought
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes from above
12 - 1 handful baby spinach or arugula leaves, optional

# How-To Steps:

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. Allow to 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 slice. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar cheese, and spinach or arugula if desired. Cover with remaining bread slices, buttered side facing 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 each sandwich in half and serve immediately.

# Expert Tips:

01 -
  • The slow-roasted tomatoes become jammy and intense, creating bursts of sweet-tart flavor that perfectly balance the creamy cheese
  • It comes together faster than you'd think since the tomatoes roast hands-free while you prep everything else
  • The combination of mozzarella and sharp cheddar gives you that perfect cheese pull with actual depth of flavor
02 -
  • Medium-low heat is non-negotiable—high heat will burn your bread before the cheese has a chance to melt through
  • Let the roasted tomatoes cool for just a few minutes before assembling, otherwise they'll make your bread soggy
  • Dont skip pressing down gently with your spatula—it helps everything meld together and ensures even contact with the pan
03 -
  • Use a cast iron skillet if you have one—the heavy, even heat creates the most evenly golden and crispy crust
  • If your roasted tomatoes release a lot of liquid during roasting, gently pat them dry with paper towels before assembling
  • Butter your bread all the way to the edges—every bite should have that buttery, golden crunch
Go Back