Roasted Tomato Pesto Grilled Cheese (Printable)

A comforting twist on the classic with caramelized roasted tomatoes, fragrant basil pesto, and gooey melted cheese between golden slices of rustic bread.

# What You Need:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4-inch thick
02 - 1 tbsp olive oil
03 - 1/4 tsp sea salt
04 - 1/4 tsp freshly ground black pepper
05 - 1/4 tsp dried oregano

→ Sandwich Assembly

06 - 4 slices rustic sourdough or country bread
07 - 2 tbsp unsalted butter, softened
08 - 2 tbsp basil pesto
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - 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 prepared baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, 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 surface.
04 - Spread 1 tbsp 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.
05 - Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4–5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice in half and serve immediately.

# Expert Suggestions:

01 -
  • The roasted tomatoes become concentrated umami bombs that elevate a simple sandwich into something restaurant worthy
  • This recipe proves that taking 60 extra minutes to roast tomatoes changes everything about the classic grilled cheese experience
02 -
  • Low and slow grilling is non negotiable because high heat burns the bread before the cheese has time to melt through all those layers
  • The roasted tomatoes can be made up to 3 days ahead and stored in the refrigerator which makes assembling these sandwiches incredibly quick
03 -
  • Let the finished sandwich rest for about 2 minutes before slicing to prevent all that glorious cheese from oozing out immediately
  • A cast iron skillet distributes heat more evenly than thinner pans giving you that perfectly uniform golden crust
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