Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes and basil pesto elevate classic grilled cheese with gooey melted cheese 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
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Handful of 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 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. Let cool slightly.
03 - Spread softened 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 of bread. Top each slice 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.
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 sandwiches in half and serve immediately.

# Expert Tips:

01 -
  • The slow roasted tomatoes add a depth of sweetness that cuts through rich, melted cheese
  • Its the kind of sandwich that makes a regular Tuesday feel like a treat
02 -
  • Low and slow heat is your friend here because high heat will burn the bread before the cheese has a chance to melt properly
  • The roasted tomatoes can be made a day ahead and stored in the refrigerator, which makes assembly incredibly quick on busy weeknights
03 -
  • If your pesto is too thick to spread easily, whisk in a teaspoon of olive oil to loosen it up
  • Mayo can be swapped for the butter on the outside of the bread for an extra crispy, golden crust that will not burn as easily
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