Roasted Tomato Pesto Grilled Cheese (Print View)

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

# 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, homemade or store-bought
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes from preparation above
12 - 1 cup baby spinach or arugula leaves, optional

# Preparation Steps:

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 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. Remove from oven and 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 the unbuttered side of each bread slice. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if desired. 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 -
  • The slow roasted tomatoes add a deep sweetness that cuts through the richness of melted cheese in a way fresh tomatoes never could.
  • It feels fancy enough for guests but uses pantry staples and comes together faster than ordering takeout.
  • The combination of two cheeses creates layers of flavor, one creamy and mild, the other sharp and bold.
  • Leftovers reheat beautifully in a skillet, crisping right back up without getting soggy.
02 -
  • Do not rush the tomato roasting, higher heat will dry them out instead of concentrating their sweetness into jammy, caramelized bites.
  • Keep the skillet heat on medium low or the bread will burn before the cheese melts, patience here is everything.
  • Softened butter spreads without tearing the bread, cold butter rips holes and leaves uneven coverage that leads to pale spots.
03 -
  • Press gently but firmly with the spatula while cooking, it helps the cheese melt evenly and keeps the layers from sliding apart.
  • Let the roasted tomatoes cool slightly before assembling so they do not make the bread soggy or melt the butter too fast.
  • Use day old bread if you have it, the slightly drier texture crisps up better and holds its structure under all that melted cheese.
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