Roasted Tomato Pesto Grilled Cheese (Printer-Friendly)

Caramelized tomatoes and fragrant pesto transform classic grilled cheese into a gourmet experience with layers of melted mozzarella and sharp cheddar.

# What You'll Need:

→ Roasted Tomatoes

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→ Sandwich Assembly

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# Direction Steps:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices on the sheet, drizzle with olive oil, and season with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, until deeply caramelized but still holding shape. Cool slightly.
02 - Spread softened butter on one side of each bread slice. Place 2 slices butter-side down on a clean work surface.
03 - Spread 1 tablespoon pesto on each unbuttered side. Layer 2 slices mozzarella, roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Top with remaining bread slices, buttered side up.
04 - Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4–5 minutes per side, pressing gently, until golden brown and cheese is completely melted.
05 - Slice sandwiches in half diagonally and serve immediately while hot.

# Expert Advice:

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  • The roasted tomatoes become concentrated little bursts of umami that perfectly cut through rich melted cheese
  • It transforms childhood comfort food into something restaurant-worthy while still being incredibly simple
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  • Medium-low heat is crucial because high heat burns the bread before the cheese has time to melt
  • The roasted tomatoes can be made ahead and stored in the refrigerator for up to a week
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  • Add a thin layer of mayonnaise instead of butter on the outside for an even crispier, more golden crust
  • Place a weight like another pan on top while cooking for restaurant-perfect pressing
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