Roasted Tomato Pesto Grilled Cheese (Print Version)

Gourmet comfort food featuring slow-roasted tomatoes, basil pesto, and melted cheese 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 - Roasted tomatoes from preparation
12 - 1 handful baby spinach or arugula leaves, optional

# How to Prepare:

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 and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized but retain their shape. 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 unbuttered side of each bottom slice. Layer 2 slices mozzarella on each, followed by roasted tomatoes, 2 slices cheddar, and spinach or arugula if desired. Top with remaining bread slices, buttered side up.
05 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in pan and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is completely melted.
06 - Slice sandwiches diagonally in half and serve immediately while cheese is still warm.

# Expert Advice:

01 -
  • The roasted tomatoes transform into concentrated bites of sweetness that balance perfectly with sharp cheddar
  • Its the kind of sandwich that makes you pause and genuinely appreciate what comfort food can be
02 -
  • Low and slow is the secret to those tomatoes, high heat will just dry them out
  • Patience with the grilling pays off, rushing over high heat burns the bread before the cheese melts
03 -
  • Let the sandwiches rest for a minute before cutting so the cheese sets slightly
  • If your pesto is thick, thin it with a teaspoon of olive oil for easier spreading
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