Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes meet basil pesto and melted cheese in this gourmet grilled cheese sandwich on rustic 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 - Roasted tomatoes from preparation
12 - Handful of baby spinach or arugula leaves, optional

# How to Make It:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the prepared 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. Allow to cool slightly.
02 - Spread softened butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean work surface.
03 - Spread 1 tablespoon pesto on each unbuttered side of the bread. Top each with 2 slices mozzarella cheese, a layer of roasted tomatoes, 2 slices sharp cheddar cheese, and spinach or arugula if desired. Cover with remaining bread slices, buttered side up.
04 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
05 - Slice each sandwich in half diagonally and serve immediately while hot.

# Expert Advice:

01 -
  • The roasted tomatoes become candy-sweet and intense, like little flavor bombs tucked inside all that melted cheese
  • Its the kind of comfort food that manages to feel fancy enough for guests but simple enough for a solo Tuesday night dinner
02 -
  • Medium-low heat is your friend here, high heat will burn the bread before the cheese has time to melt properly
  • The roasted tomatoes can be made a day ahead and stored in the refrigerator, which actually makes this sandwich come together incredibly quickly
03 -
  • If your tomatoes seem especially juicy, pat them dry with paper towels before roasting to concentrate the flavor even more
  • Use a cast iron skillet if you have one, it maintains heat beautifully and creates the most even, golden crust imaginable
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