Roasted Tomato Pesto Grilled Cheese (Printable)

Gourmet grilled cheese with slow-roasted tomatoes, basil pesto, and melted mozzarella and cheddar on rustic sourdough bread.

# Ingredient List:

→ 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 - Handful of baby spinach or arugula leaves, optional

# How to Prepare:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the prepared baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and oregano.
02 - Roast for 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still hold their shape. Remove from oven and let cool slightly.
03 - Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface. 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 desired. Cover with remaining bread slices, buttered side up.
04 - 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.
05 - Slice each sandwich in half and serve immediately.

# Expert Suggestions:

01 -
  • The roasted tomatoes develop this incredible sweetness that cuts through the rich cheese like nothing else
  • It takes a simple comfort food and makes it feel like something you'd order at a fancy bistro but better
02 -
  • The tomatoes might look done before they really are so trust the full roasting time for that deep flavor
  • Medium low heat is crucial for grilled cheese too hot and the bread burns before the cheese melts
03 -
  • Pat your roasted tomatoes gently with paper towels before assembling so the bread stays crisp
  • Use a cast iron skillet if you have one for the most even browning
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