Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes, basil pesto, and melted cheese on rustic bread create an elevated comfort food sandwich.

# 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 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. 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 each unbuttered side of bread. Layer 2 slices mozzarella, roasted tomato slices, 2 slices cheddar, and spinach or arugula if desired on each slice. Cover with remaining bread slices, buttered side up.
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 - Slice each sandwich in half and serve immediately.

# Expert Advice:

01 -
  • The combination of mozzarella and sharp cheddar provides the perfect balance of melt and flavor.
  • Slow-roasting tomatoes concentrates their sugars for a deep, caramelized taste.
  • Sourdough bread offers a sturdy, tangy base that crisps up beautifully in the pan.
02 -
  • Use softened butter to ensure it spreads evenly without tearing the bread.
  • Press down gently with a spatula during grilling to help the ingredients bond and heat through.
  • Check pesto labels for allergens like nuts or extra dairy if you have dietary restrictions.
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