Roasted Tomato Pesto Grilled Cheese (Print Version)

Slow-roasted tomatoes, basil pesto, and melted cheese create a gourmet sandwich perfect for lunch or light dinner.

# Components:

→ 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 preparation
12 - Handful of baby spinach or arugula leaves, optional

# Method:

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 deeply caramelized but still holding their shape. Allow to 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 tablespoon pesto on unbuttered side of each bread slice. Layer 2 slices mozzarella, roasted tomato layer, 2 slices cheddar, and spinach or arugula if desired. Cover with remaining bread slices, buttered side up.
05 - Heat 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 completely melted.
06 - Slice sandwiches in half diagonally and serve immediately.

# Expert Advice:

01 -
  • It tastes like a restaurant splurge but uses ingredients you probably already have.
  • The roasted tomatoes add a sweetness and depth that raw tomatoes just can't match.
  • It's impressive enough for guests but easy enough for a solo weeknight dinner.
  • The combination of mozzarella and sharp cheddar gives you both melt and flavor.
02 -
  • Don't rush the tomato roasting, I tried it once at a higher temperature to save time and ended up with dried-out slices instead of jammy ones.
  • Use medium-low heat when grilling, too high and the bread burns before the cheese melts, leaving you with a sad, half-melted sandwich.
  • Softened butter is key, cold butter tears the bread and spreads unevenly, and mayonnaise just doesn't taste right to me on this one.
03 -
  • Press down gently with the spatula while grilling to help the cheese melt evenly and the layers stick together.
  • Let the roasted tomatoes cool for a few minutes before assembling, otherwise the heat can make the bread soggy.
  • If you're making multiple sandwiches, keep the finished ones warm in a 200°F oven while you cook the rest.
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