Roasted Tomato Pesto Grilled Cheese (Printable)

Caramelized tomatoes and basil pesto transform classic grilled cheese into a gourmet sandwich experience.

# 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 Assembly

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 (prepared above)
12 - Handful of baby spinach or arugula leaves (optional)

# Directions:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices in a single layer. Drizzle with olive oil, then sprinkle evenly with sea salt, black pepper, and dried oregano. Roast for 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still maintain their shape. Remove from oven and let cool slightly.
02 - Spread softened butter evenly on one side of each bread slice. Place two slices butter-side down on a clean work surface.
03 - Spread 1 tablespoon of basil pesto on each unbuttered side of the bread. Layer 2 slices of mozzarella cheese on top, followed by a portion of roasted tomatoes, then 2 slices of sharp cheddar. Add spinach or arugula if desired. Top with remaining bread slices, butter-side facing up.
04 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook for 4 to 5 minutes per side, pressing gently with a spatula, until bread is golden brown and cheese is completely melted.
05 - Transfer sandwiches to a cutting board. Slice each sandwich in half diagonally and serve immediately while hot.

# Expert Suggestions:

01 -
  • The roasted tomatoes become concentrated bursts of sweet umami that balance perfectly with melted cheese
  • This sandwich feels fancy enough for company but comes together in under 15 minutes of active work
02 -
  • Low and slow roasting is non-negotiable here because high heat will dry out the tomatoes before they can develop that jammy consistency
  • Buttering the bread generously prevents burning and ensures the exterior becomes shatteringly crisp
03 -
  • Mayo makes an excellent alternative to butter for the exterior of the bread and creates an even crispier crust
  • A sprinkle of grated parmesan on the buttered bread before grilling adds an extra crispy, cheesy layer
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