Roasted Tomato Pesto Grilled Cheese (Printable)

Caramelized tomatoes and basil pesto elevate this comforting sandwich with layers of melted mozzarella and cheddar on rustic bread.

# What You Need:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4-inch thick
02 - 1 tbsp olive oil
03 - 1/4 tsp sea salt
04 - 1/4 tsp freshly ground black pepper
05 - 1/4 tsp dried oregano

→ Sandwich Assembly

06 - 4 slices rustic sourdough or country bread
07 - 2 tbsp unsalted butter, softened
08 - 2 tbsp basil pesto (homemade or store-bought)
09 - 4 slices mozzarella cheese (or provolone or fontina)
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes (from above)
12 - 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 the prepared baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, until tomatoes are deeply caramelized but still hold their shape. Let cool slightly.
03 - Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface.
04 - Spread 1 tbsp pesto on each unbuttered side. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Cover with remaining bread slices, buttered side up.
05 - Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4–5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice in half and serve immediately.

# Expert Suggestions:

01 -
  • The roasted tomatoes become candy-like and intense, transforming the ordinary into something extraordinary
  • Its the kind of comfort food that makes even a terrible day feel suddenly manageable
02 -
  • Pat your roasted tomatoes gently with paper towels before assembling to prevent soggy bread
  • Medium-low heat is your friend because high heat burns the bread before the cheese melts
03 -
  • Use a cast iron skillet if you have one because it creates the most even, beautiful golden crust
  • Weigh down your sandwich with a heavy pan or bacon press for that authentic pressed sandwich feel
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