Roasted Tomato Pesto Grilled Cheese (Printable View)

A gourmet grilled cheese featuring slow-roasted tomatoes, basil pesto, and melted cheese 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, homemade or store-bought
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes from preparation
12 - Optional: handful of baby spinach or arugula leaves

# How To Make It:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper.
02 - Arrange tomato slices on prepared baking 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. 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 each sandwich in half and serve immediately.

# Expert Advice:

01 -
  • Gourmet Flavors: Slow-roasting the tomatoes intensifies their sweetness and adds a rich umami depth.
  • Perfect Texture: The combination of rustic sourdough and a dual-cheese blend ensures a crispy exterior and a gooey, melted center.
  • Simple Sophistication: It is easy to prepare yet feels like a dish served at a high-end bistro.
02 -
  • Temperature Control: Cooking over medium-low heat is essential for the perfect melt without burning the sourdough.
  • Tomato Prep: Ensure the tomato slices are uniform in thickness so they roast evenly in the oven.
  • Fresh Greens: Adding the optional spinach or arugula provides a fresh bite that balances the heavy cheese.
Go Back