Roasted Tomato Pesto Grilled Cheese (Printable)

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 - Roasted tomatoes from preparation
12 - Handful of baby spinach or arugula leaves, optional

# How-To 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 tomatoes are deeply caramelized but still hold their 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 the unbuttered side of each bread slice. 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 facing up.
05 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in skillet and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice each sandwich in half and serve immediately.

# Expert Suggestions:

01 -
  • The roasted tomatoes become candy-sweet and deeply savory, creating an incredible depth of flavor
  • That combination of melted mozzarella and sharp cheddar gives you the perfect pull and bite
  • It is the kind of comfort food that feels fancy enough for company but easy enough for a Tuesday night
02 -
  • Low and slow roasting is the secret to tomatoes that actually taste like something, so do not rush this step
  • Medium-low heat prevents the bread from burning before the cheese has a chance to melt completely
  • Let the sandwiches rest for about 30 seconds after grilling so the cheese sets slightly and does not ooze out everywhere when you cut them
03 -
  • Weigh the sandwiches down with a heavy pan or press for restaurant-style grilling marks
  • If the cheese is not melting, tent the pan with foil for the last minute of cooking
  • Room temperature cheese melts more evenly than cold cheese straight from the refrigerator
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