Roasted Tomato Pesto Grilled Cheese (Printable)

Slow-roasted tomatoes and basil pesto meet melted mozzarella and cheddar on buttery sourdough for an elevated comfort classic.

# 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 (homemade or store-bought)
09 - 4 slices mozzarella cheese
10 - 4 slices sharp cheddar cheese
11 - handful of 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 sheet, drizzle with olive oil, and sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, until deeply caramelized but still holding their shape. Let cool slightly.
02 - Spread softened butter on one side of each bread slice. Place 2 slices butter-side down on a clean surface.
03 - Spread 1 tbsp pesto on each unbuttered side. Layer with 2 slices mozzarella, roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Top with remaining bread slices, buttered side up.
04 - Heat a large skillet or griddle over medium-low heat. Cook sandwiches 4–5 minutes per side, pressing gently, until golden brown and cheese is fully melted. Slice in half and serve immediately.

# Expert Advice:

01 -
  • The slow-roasted tomatoes become umami bombs that elevate everything they touch
  • This sandwich manages to feel gourmet while still being the ultimate comfort food
02 -
  • Pat your roasted tomatoes with paper towels before assembling or your bread will get soggy
  • Keep the heat medium-low so the cheese melts completely before the bread burns
03 -
  • Roast extra tomatoes and keep them in the fridge for up to a week
  • Use a cast iron skillet for the most evenly crisped bread
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