Roasted Tomato Pesto Grilled Cheese (Printable Format)

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

# What's Needed:

→ 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

# How To Make It:

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 retain their shape. Remove from oven and let cool slightly.
03 - Spread softened butter on one side of each bread slice. Place 2 slices buttered side down on work 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 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 each sandwich in half and serve immediately.

# Expert Advice:

01 -
  • The roasted tomatoes become candy-sweet and intense, elevating a simple sandwich into something restaurant-worthy
  • Its the perfect balance of tangy pesto, rich melted cheese, and that satisfying crunch from buttery sourdough
02 -
  • Medium-low heat is your friend here because high heat will burn the bread before the cheese has time to melt into gooey perfection
  • The roasted tomatoes can be made ahead and kept in the refrigerator for up to a week, actually developing even more flavor
03 -
  • Room temperature cheese melts more evenly and quickly than cold cheese straight from the refrigerator
  • If your pesto is too thick, thin it slightly with a teaspoon of olive oil for easier spreading
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