Roasted Tomato Pesto Grilled Cheese (Print Version)

Gourmet grilled cheese with slow-roasted tomatoes, basil pesto, and melted mozzarella and cheddar 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
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Handful of baby spinach or arugula leaves, optional

# How-To Steps:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the prepared baking sheet. Drizzle with olive oil, 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. Let cool slightly.
02 - Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface. Spread 1 tablespoon pesto on each unbuttered side. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Cover with remaining bread slices, buttered side up.
03 - 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.
04 - Slice in half and serve immediately.

# Expert Advice:

01 -
  • The slow-roasted tomatoes become sweet and intense, creating this incredible depth that regular grilled cheese just cannot match
  • This is the kind of comfort food that feels fancy enough for guests but comes together easily on a weeknight
02 -
  • I learned the hard way that high heat will burn your bread before the cheese has time to melt properly, so patience with medium-low heat is absolutely essential
  • Soggy sandwiches happen when you skip the parchment paper or crowd the tomatoes too close together while roasting
03 -
  • Smoked gouda or gruyère add incredible depth if you want to branch out from the traditional cheddar
  • A well-seasoned cast iron skillet will give you the most even browning and requires less butter
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