Roasted Tomato Pesto Grilled Cheese (Printable)

Golden crispy sandwich with slow-roasted tomatoes, basil pesto, and gooey melted cheese on rustic bread.

# What You Need:

→ Roasted Tomatoes

01 -
02 -
03 -
04 -
05 -

→ Sandwich Assembly

06 -
07 -
08 -
09 -
10 -
11 -

# How to Make It:

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 season with sea salt, black pepper, and dried oregano. Roast for 50-60 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 basil pesto on the unbuttered side of each bread slice. Layer 2 slices mozzarella cheese, followed by roasted tomatoes, then 2 slices sharp cheddar cheese. Add spinach or arugula if desired. Top with remaining bread slices, buttered side facing up.
04 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook for 4-5 minutes per side, pressing gently with a spatula. Flip carefully and continue cooking until golden brown and cheese is completely melted.
05 - Transfer sandwiches to a cutting board. Slice diagonally in half and serve immediately while hot and cheesy.

# Expert Suggestions:

01 -
  • The roasted tomatoes become candy-sweet and umami-rich, transforming ordinary grilled cheese into something that feels restaurant special
  • Its the perfect balance of gooey, crispy, and fresh with hardly any active cooking time
02 -
  • Low and slow is the secret to getting that golden crust without burning the bread before the cheese melts
  • The tomatoes can be roasted up to 3 days ahead and stored in the fridge, which actually makes weeknight sandwiches come together in minutes
03 -
  • Pat the roasted tomatoes gently with paper towels before assembling to prevent soggy bread
  • Use a cast-iron skillet if you have one, it creates the most even, golden crust
Go Back