Roasted Tomato Pesto Grilled Cheese (Printable)

Golden sourdough with caramelized tomatoes, pesto, and melted cheeses

# 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 (homemade or store-bought)
09 - 4 slices mozzarella cheese (or provolone or fontina)
10 - 4 slices sharp cheddar cheese
11 - Roasted tomatoes (from above)
12 - Optional: handful of baby spinach or arugula leaves

# How-To 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, 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:

01 -
  • The roasted tomato pesto combo creates layers of flavor that feel fancy but come together in under 15 minutes of active work
  • Something magical happens when that pesto hits the warm cheese and the tomato juices soak into the bread
02 -
  • Low and slow is the secret to those tomatoes, don't rush the roasting process or you'll miss all the caramelized flavor
  • Medium-low heat on the stove is crucial, high heat burns the bread before the cheese has a chance to melt
03 -
  • If your pesto is thick, stir in a teaspoon of olive oil so it spreads easily across the bread
  • Use good cheese, seriously, the cheap stuff won't melt properly and you deserve better
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