Roasted Tomato Pesto Grilled Cheese

It started as a way to use up an abundance of summer tomatoes from my garden, but this sandwich has completely ruined regular grilled cheese for me forever. The slow roasting concentrates the tomatoes into something sweet and intense, almost like candy, and when that meets pesto and melted cheese, something magical happens.

My sister was visiting last fall when I first made these, and she literally ate three in one sitting while standing at the counter. She kept saying she would stop after one more, then another, then another. Now whenever she visits, this is the first thing she requests.

Ingredients

• Large ripe tomatoes: Vine ripened tomatoes work best here since roasting amplifies their natural sweetness
• Olive oil: This helps the tomatoes caramelize rather than just dry out in the oven
• Rustic sourdough or country bread: Something sturdy that wont get soggy when layered with all those juicy components
• Unsalted butter: Buttering the outside creates that irresistible golden crunch we all love in grilled cheese
• Basil pesto: Homemade brings the brightest flavor but store bought works perfectly fine on busy weeknights
• Mozzarella cheese: This provides the classic melt and stretch factor
• Sharp cheddar cheese: The sharpness cuts through the richness and adds that extra flavor kick
• Baby spinach or arugula: This adds freshness and a slight peppery bite that balances all the cheese

Instructions

Roast the tomatoes low and slow:

Preheat your oven to 300F and line a baking sheet with parchment paper. Arrange your tomato slices in a single layer and drizzle them with olive oil, then sprinkle with sea salt, black pepper, and dried oregano. Roast them for 50 to 60 minutes, flipping halfway through, until they are deeply caramelized but still hold their shape.

Prep your bread canvas:

Spread softened butter on one side of each bread slice, then place two slices butter side down on your work surface. Spread a generous tablespoon of pesto on each unbuttered side.

Build your sandwich masterpiece:

Layer two slices of mozzarella, your roasted tomatoes, two slices of sharp cheddar, and a handful of spinach or arugula on the pesto covered bread. Top with the remaining bread slices, buttered side facing up.

Grill to golden perfection:

Heat a large skillet or griddle over medium low heat and add your sandwiches. Cook for 4 to 5 minutes per side, pressing gently with your spatula, until both sides are golden brown and the cheese is completely melted.

Serve immediately:

Slice each sandwich in half diagonally and serve while the cheese is still hot and gooey.

Save

This has become my go to comfort food, especially on rainy Sundays when I want something warm and satisfying but not too heavy.

Making Ahead

The roasted tomatoes can be made up to three days in advance and stored in the refrigerator. They actually develop even more flavor after a day or two, making this a perfect meal prep component.

Cheese Variations

While mozzarella and cheddar is my favorite combination, I have also used gruyère for extra nuttiness, provolone for a milder flavor, or pepper jack when I want a bit of heat. Just stick to cheeses that melt well.

Serving Suggestions

A simple green salad with vinaigrette cuts through the richness beautifully, or serve alongside a cup of tomato soup for the ultimate comfort meal. This also pairs surprisingly well with a crisp white wine or light beer.

• Try sun dried tomato pesto instead of regular basil for an even more intense tomato flavor
• Add a pinch of red pepper flakes to the pesto for subtle heat
• Use gluten free bread if needed, the sandwich still comes out delicious

Save

There is something deeply satisfying about taking that first bite and hearing the crunch of perfectly toasted bread followed by all that melty, roasted tomato goodness inside.

Recipe FAQs

→ Why roast the tomatoes instead of using fresh ones?

Slow-roasting concentrates the natural sugars in tomatoes, creating deep caramelized flavors and a chewy texture that holds up beautifully between melted cheese. Fresh tomatoes would release too much moisture and make the bread soggy.

→ Can I use store-bought pesto?

Absolutely! Store-bought basil pesto works perfectly well. Look for a high-quality brand with good olive oil and fresh basil flavor. You can also experiment with sun-dried tomato pesto for an extra layer of tomato intensity.

→ What cheese combinations work best?

The classic pairing of mozzarella and sharp cheddar provides both excellent meltability and robust flavor. Fontina, Gruyère, provolone, or smoked Gouda are all fantastic alternatives. Choose cheeses that melt well to ensure that perfect gooey texture.

→ How do I get the crispiest bread?

Use softened butter and spread it evenly to the edges. Cook over medium-low heat to allow the cheese to melt completely before the bread burns. A cast iron skillet or griddle provides even heating for the best results. Don't press too hard—you want to maintain the bread's structure.

→ Can I make these ahead of time?

You can roast the tomatoes up to 3 days in advance and store them in the refrigerator. The sandwiches are best cooked fresh, but you can assemble them and wrap tightly in the refrigerator for a few hours before cooking.

→ What should I serve with these sandwiches?

A crisp green salad with vinaigrette cuts through the richness perfectly. A cup of warm tomato soup creates the ultimate comfort meal. Pickles, coleslaw, or a simple fruit salad also make excellent sides.