Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes and basil pesto layered with melted mozzarella and sharp cheddar between buttery sourdough slices.

# What You'll Need:

→ Roasted Tomatoes

01 - 2 large ripe tomatoes, sliced 1/4-inch thick
02 - 1 tbsp olive oil
03 - 1/4 tsp sea salt
04 - 1/4 tsp freshly ground black pepper
05 - 1/4 tsp dried oregano

→ Sandwich Assembly

06 - 4 slices rustic sourdough or country bread
07 - 2 tbsp unsalted butter, softened
08 - 2 tbsp basil pesto
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - Handful 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 50–60 minutes, flipping halfway, until deeply caramelized but still holding shape. Cool slightly.
02 - Spread butter on one side of each bread slice. Place 2 slices buttered side down on a clean surface. Spread 1 tbsp pesto on each unbuttered side.
03 - Top each pesto-covered slice 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.
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 fully melted.
05 - Slice sandwiches in half and serve immediately while hot and melty.

# Expert Tips:

01 -
  • The roasted tomatoes become jammy and intense, adding a depth that regular grilled cheese simply cannot match
  • Its the kind of comfort food that feels fancy enough for guests but easy enough for a solo dinner
02 -
  • Low and slow roasting is what transforms the tomatoes. Rush this step and you will miss the jammy sweetness that makes this sandwich special.
  • Medium-low heat for grilling ensures the bread crisps perfectly and the cheese melts completely before the exterior burns.
03 -
  • Patting the tomato slices dry before roasting helps them caramelize better rather than steam in their own moisture.
  • A cast iron skillet creates the most beautiful, even crust on the bread.
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