Roasted Tomato Pesto Grilled Cheese

The first time I slow-roasted tomatoes for grilled cheese, my kitchen smelled like an Italian restaurant. I was experimenting with what seemed like an unnecessary step, but those caramelized tomato slices transformed everything. Now I cannot make grilled cheese any other way.

My roommate walked in while these were roasting and demanded to know what smelled so incredible. We ate them standing at the counter, burning our fingers because we could not wait for them to cool down.

Ingredients

• 2 large ripe tomatoes: Choose tomatoes that yield slightly to pressure and feel heavy for their size
• 1 tbsp olive oil: This helps the tomatoes caramelize and develop that deep, concentrated flavor
• 1/4 tsp sea salt: Draws out moisture and intensifies the tomato essence as they roast
• 1/4 tsp freshly ground black pepper: Adds a subtle warmth that complements the sweet roasted tomatoes
• 1/4 tsp dried oregano: Echoes Italian notes without overpowering the other ingredients
• 4 slices rustic sourdough or country bread: Sturdy enough to hold generous fillings without getting soggy
• 2 tbsp unsalted butter: Room temperature butter spreads more evenly and creates that perfect golden crust
• 2 tbsp basil pesto: Homemade pesto yields the brightest flavor, but a good store-bought version works beautifully
• 4 slices mozzarella cheese: Provides that incredible melted cheese pull in every bite
• 4 slices sharp cheddar cheese: Adds the necessary punch and tang to cut through the richness
• Handful of baby spinach or arugula: Optional but adds a fresh, peppery contrast to the warm filling

Instructions

Roast the tomatoes until golden:

Preheat oven to 300°F (150°C) and line a baking sheet with parchment paper. Arrange tomato slices in a single layer, drizzle with olive oil, then sprinkle with salt, pepper and oregano. Roast 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized and slightly shriveled but still hold their shape.

Assemble the sandwiches:

Spread softened butter on one side of each bread slice. Place two slices butter-side down and spread 1 tbsp pesto on each upward-facing slice. Layer 2 slices mozzarella, roasted tomatoes, 2 slices cheddar and greens if using, then top with remaining bread slices, butter-side up.

Grill to golden perfection:

Heat a large skillet or griddle over medium-low heat. Place sandwiches in the pan and cook 4 to 5 minutes per side, pressing gently with a spatula, until bread is deeply golden and cheese is completely melted.

Serve immediately:

Cut each sandwich in half diagonally and serve while the cheese is still molten and the bread is at its crispest.

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This recipe has become my go-to when I need comfort food that feels a little special. Something about the combination of warm roasted tomatoes and melted cheese just makes everything better.

Cheese Selection Matters

While the recipe calls for mozzarella and sharp cheddar, I have discovered that fontina brings an incredible nuttiness that pairs beautifully with the roasted tomatoes. Provolone adds a pleasant smokiness, and gruyère creates the most luxurious melt. Just make sure at least one of your cheeses has some sharpness to cut through the richness.

Making It Ahead

You can roast the tomatoes up to three days in advance and store them in an airtight container in the refrigerator. In fact, the flavors develop even more after a day. I often make a double batch just to keep roasted tomatoes on hand for quick sandwiches, pasta, or even just eating straight from the container.

Perfect Pairings

A crisp green salad with an acidic vinaigrette cuts through the richness perfectly, while a cup of tomato soup makes this feel like the ultimate comfort meal. I have also served these alongside a simple bowl of minestrone for a dinner that feels like it came from an Italian restaurant.

• Roast extra tomatoes and keep them in your refrigerator for emergency sandwich situations
• If the bread is toasting too quickly before the cheese melts, tent the pan with foil for the last minute or two
• Let the sandwiches rest for about 60 seconds after grilling so the cheese sets slightly and does not ooze out completely when you cut them

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There is something deeply satisfying about the way the pesto, roasted tomatoes and melted cheese come together in each bite. This sandwich has become my definition of comfort food elevated.

Recipe Questions & Answers

→ Why roast the tomatoes first?

Roasting concentrates the tomatoes' natural sugars and creates deep caramelized flavors that balance beautifully with the rich cheese and fragrant pesto.

→ What type of bread works best?

Rustic sourdough or country bread provides sturdy structure and excellent flavor. The bread needs to hold up to the generous filling without becoming soggy.

→ Can I make this ahead?

Roast tomatoes up to 2 days ahead and store refrigerated. Assemble sandwiches just before cooking for the best texture and melt.

→ What cheese combinations work well?

The mozzarella provides exceptional melt while sharp cheddar adds bite. Try provolone, fontina, gruyère, or smoked gouda for different flavor profiles.

→ How do I get perfectly crispy results?

Cook over medium-low heat to allow the cheese to melt completely before the bread burns. Press gently with a spatula for even contact and golden crunch.

→ What pairs well with this sandwich?

A crisp green salad with vinaigrette cuts through the richness. Tomato soup creates a classic pairing, or serve alongside a cup of minestrone.