Roasted Tomato Pesto Grilled Cheese (Printable Page)

Slow-roasted tomatoes and basil pesto elevate this gourmet grilled cheese with melted mozzarella and cheddar on rustic sourdough bread.

# 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, homemade or store-bought
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

# Step-by-Step Guide:

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, 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 surface.
04 - 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.
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 Tips:

01 -
  • The roasted tomatoes become sweet and intense, like sundried tomatoes but with this fresh juiciness that makes the sandwich feel special
  • That combination of melty mozzarella and sharp cheddar creates this perfect balance of creamy and tangy that I have not found elsewhere
02 -
  • Low and slow heat is crucial here because high heat will burn the bread before the cheese has time to melt through all those layers
  • The roasted tomatoes can be made up to three days ahead and kept in the refrigerator, which actually makes this sandwich come together incredibly fast on busy days
03 -
  • If your roasted tomatoes release a lot of liquid during roasting, gently pat them dry with paper towels before assembling your sandwich
  • A cast iron skillet distributes heat beautifully and creates that restaurant style golden crust I am always chasing
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