Roasted Tomato Pesto Grilled Cheese (Printable version)

Crispy sourdough layered with slow-roasted tomatoes, fragrant basil pesto, and gooey melted mozzarella and cheddar for a gourmet twist on comfort food.

# What You 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)

# Step-by-step guide:

01 - Preheat oven to 300°F. Line a baking sheet with parchment paper. Arrange tomato slices in a single layer. Drizzle with olive oil, then sprinkle with sea salt, black pepper, and dried oregano. Roast for 50-60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still maintain their shape. Remove from oven and let cool slightly.
02 - Spread softened butter evenly on one side of each bread slice. Place two slices butter-side down on a clean work surface. Spread 1 tbsp basil pesto on each unbuttered side. Layer with 2 slices mozzarella, roasted tomatoes, 2 slices cheddar, and spinach or arugula if desired. Top with remaining bread slices, butter-side up.
03 - Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook for 4-5 minutes per side, pressing gently with a spatula. Cook until bread is golden brown and crispy, and cheese is completely melted. Transfer to a cutting board, slice diagonally in half, and serve immediately.

# Expert Advice:

01 -
  • The slow roasted tomatoes become sweet and concentrated, creating this incredible depth that regular grilled cheese just doesnt have
  • Its the perfect balance of nostalgic comfort food and something that feels special enough for company
02 -
  • Dont rush the tomato roasting process, that low and slow heat is what transforms them into something extraordinary
  • Keep the heat medium low when grilling so the bread crisps perfectly before the cheese has time to ooze out
03 -
  • Room temperature cheese melts more evenly and quickly, so take it out of the fridge while the tomatoes roast
  • Use a good quality bread, it really does make a noticeable difference in the final sandwich
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