Roasted Tomato Pesto Grilled Cheese (Printable Version)

A comforting sandwich with caramelized tomatoes, pesto, and melted cheese on sourdough.

# What You'll Need:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4-inch thick
02 - 1 tbsp olive oil
03 - 1/4 tsp sea salt
04 - 1/4 tsp freshly ground black pepper
05 - 1/4 tsp dried oregano

→ Sandwich Assembly

06 - 4 slices rustic sourdough or country bread
07 - 2 tbsp unsalted butter, softened
08 - 2 tbsp basil pesto (homemade or store-bought)
09 - 4 slices mozzarella cheese (or provolone or fontina)
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes (prepared above)
12 - Handful of baby spinach or arugula leaves (optional)

# Steps:

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

# Expert Advice:

01 -
  • The roasted tomatoes become sweet and intense, like candy from the oven
  • That pesto and melty cheese combo is basically instant comfort
  • Takes regular grilled cheese and elevates it into something you would actually serve to friends
02 -
  • Roasting tomatoes ahead of time is a game-changer—make extra and keep them in the fridge for impromptu sandwiches
  • Medium-low heat is your friend here or you will burn the bread before the cheese melts
03 -
  • Cheese that is at room temperature melts faster and more evenly
  • A well-warmed skillet with even heat distribution prevents hot spots that burn the bread
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