Roasted Tomato Pesto Grilled Cheese (Printable Version)

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

# 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

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 above
12 - 1 handful baby spinach or arugula leaves, optional

# How To Make:

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 to 60 minutes, flipping halfway through, 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 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 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 to 5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice in half and serve immediately.

# Cooking Tips:

01 -
  • The roasted tomatoes become like candy, adding an intensity you cant get from fresh tomatoes alone
  • Two cheeses means you get the perfect balance of melt and sharp flavor
  • Its the kind of meal that makes rainy afternoons feel cozy and intentional
02 -
  • Don't rush the roasting process. Those tomatoes need time to concentrate their sugars and develop that jammy texture.
  • Medium-low heat is your friend. High heat will burn the bread before the cheese has a chance to melt completely.
  • The roasted tomatoes can be made ahead and kept in the refrigerator for up to three days.
03 -
  • If your bread is fresh and soft, lightly toast it before building the sandwich. This prevents sogginess and ensures the bread holds up to all those toppings.
  • Use a mixture of grated and sliced cheese for the ultimate melt. Grated cheese melts faster and binds everything together.
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