Roasted Tomato Pesto Grilled Cheese (Printable Version)

A gourmet twist on classic grilled cheese with slow-roasted tomatoes, basil pesto, and melted cheese on rustic bread.

# What You 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 - Handful of baby spinach or arugula leaves, optional

# Step-by-Step:

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 butter on one side of each bread slice. Place 2 slices with buttered side down on a clean work surface.
04 - Spread 1 tablespoon pesto on the unbuttered side of each bread slice. Top each with 2 slices mozzarella cheese, 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 Advice:

01 -
  • Gourmet Flavor: Slow-roasting the tomatoes transforms them into deeply caramelized gems that elevate the entire sandwich.
  • Perfect Texture: The combination of rustic sourdough and a blend of mozzarella and sharp cheddar ensures a satisfying crunch and an epic cheese pull.
  • Simple Sophistication: It uses easy-to-find ingredients to create a meal that feels like it came straight from a gourmet café.
02 -
  • Low and Slow: Always cook your grilled cheese over medium-low heat. This ensures the rustic bread becomes perfectly golden and crispy without burning before the cheese has a chance to fully melt.
  • Tomato Prep: Don't skip flipping the tomatoes halfway through the roasting process; this ensures they caramelize evenly on both sides.
  • Gentle Pressure: Pressing the sandwich gently with a spatula while it cooks helps the ingredients meld together and improves heat distribution.
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