Roasted Tomato Pesto Grilled Cheese (Printable)

Gourmet grilled cheese with slow-roasted tomatoes, basil pesto, and melted mozzarella and cheddar on rustic sourdough 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 - Roasted tomatoes from preparation
12 - 1 handful baby spinach or arugula leaves, optional

# Directions:

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. Let cool slightly.
03 - Spread 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. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if desired. Cover with remaining bread slices, buttered side 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 in half and serve immediately.

# Expert Advice:

01 -
  • The roasted tomatoes become like candy, adding this incredible sweet-savory depth that regular grilled cheese just cant match
  • That crispy sourdough exterior against the gooey cheese and tender tomatoes creates the most satisfying texture contrast
02 -
  • The first time I made this, I rushed the tomato roasting at 400°F and ended up with burnt edges and raw centers
  • Buttering your bread to the very edges prevents any sad dry spots where the cheese can escape during melting
03 -
  • If your bread is particularly thick, tent the sandwich with foil for the last minute of cooking to ensure cheese melts completely
  • A cast iron skillet distributes heat more evenly than stainless steel, giving you that perfectly golden crust
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