Roasted Tomato Pesto Grilled Cheese (Printer View)

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

# Method Steps:

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 and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until deeply caramelized yet retaining 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 unbuttered side of each bread slice. Layer 2 slices mozzarella, roasted tomato slices, 2 slices cheddar, and spinach or arugula if desired on each base. Top with remaining bread slices, buttered side up.
05 - Heat 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 completely melted.
06 - Slice sandwiches in half and serve immediately.

# Expert Advice:

01 -
  • The slow roasted tomatoes taste like summer concentrate, sweet and jammy without any fuss.
  • You get restaurant quality flavor with ingredients you probably already have sitting around.
  • It's fancy enough for company but easy enough to make on a random Tuesday night.
  • The cheese pull is ridiculously satisfying and the pesto adds this herby brightness that cuts through all that richness.
02 -
  • Don't rush the tomato roasting, high heat will just dry them out instead of concentrating their sweetness.
  • Keep your skillet heat on the lower side or the bread will burn before the cheese melts, I learned this the hard way.
  • If your pesto tastes a little flat, stir in a squeeze of lemon juice to wake it up.
03 -
  • Press down gently with your spatula while grilling to help the cheese melt faster and bind everything together.
  • Let the sandwich rest for a minute after cooking so the cheese sets slightly and doesn't all slide out when you cut it.
  • Use a heavy skillet or even a panini press if you have one, the weight helps create an even crust.
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