Roasted Tomato Pesto Grilled Cheese (Printer-friendly)

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

# Ingredient List:

→ 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 - 1/2 cup baby spinach or arugula leaves (optional)

# Directions:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the prepared 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.
02 - Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface. 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.
03 - 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.
04 - Slice each sandwich in half and serve immediately.

# Expert Tips:

01 -
  • Slow-roasted tomatoes provide a deep, caramelized sweetness that elevates the sandwich.
  • The combination of mozzarella and sharp cheddar offers the perfect balance of stretch and flavor.
  • Fresh basil pesto adds an herbaceous brightness to every bite.
  • It is a simple yet sophisticated vegetarian meal.
02 -
  • Always cook on medium-low heat to ensure the cheese melts completely before the bread gets too dark.
  • Don't skip the roasting step; it removes excess moisture from the tomatoes so the bread stays crispy.
  • Check your pesto label for allergens like nuts or extra dairy to ensure it fits your dietary requirements.
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