Roasted Tomato Pesto Grilled Cheese (Printable)

Crispy sourdough loaded with slow-roasted tomatoes, basil pesto, and melted cheese for the ultimate comfort sandwich.

# What You'll Need:

→ Roasted Tomatoes

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→ Sandwich Assembly

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# How To Make It:

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 50-60 minutes, flipping halfway, 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 surface.
04 - Spread 1 tbsp 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 4-5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
06 - Slice in half and serve immediately.

# Expert Tips:

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  • The roasted tomatoes add this incredible depth that canned tomatoes or fresh ones just cant achieve
  • Its the kind of sandwich that makes people pause mid bite and genuinely ask what you put in it
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  • Do not rush the tomato roasting step since this is where all the deep flavor develops
  • Medium low heat is crucial so the bread gets golden and crispy before the cheese burns
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  • Do not skip the parchment paper since roasted tomatoes can stick and be difficult to remove
  • Let the tomatoes cool slightly before assembling so they do not make the bread soggy
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