Roasted Tomato Pesto Grilled Cheese

The first time I made roasted tomato pesto grilled cheese, it was a rainy Sunday and I was craving something that felt like a hug in food form. I had tomatoes sitting on the counter that needed using, and suddenly the idea hit me to slow roast them until they became almost candy like. The smell that filled my kitchen was incredible, and when I took that first bite, I knew this wasnt just another sandwich anymore.

Last month, my friend Sarah came over for what was supposed to be a quick lunch, and she ended up sitting at my counter for two hours while we devoured these sandwiches and talked about everything. The way the pesto mingles with the roasted tomatoes and three different cheeses creates these layers of flavor that make you want to slow down and savor every bite. Now whenever she visits, she gives me that look that means Im making these again.

Ingredients

• Large ripe tomatoes: Choose tomatoes that give slightly when pressed, they roast down beautifully and become naturally sweet
• Olive oil: This helps the tomatoes caramelize and keeps them from drying out in the oven
• Sea salt and black pepper: Simple seasoning that enhances the tomatoes natural flavors as they concentrate
• Dried oregano: Adds an Italian inspired note that bridges the tomatoes and pesto
• Rustic sourdough bread: The sturdy texture holds up well to all the fillings without getting soggy
• Unsalted butter: Buttering the bread exterior creates that perfect golden crispy crust
• Basil pesto: Homemade or store bought adds fresh herb flavor and a garlicky kick
• Mozzarella cheese: Provides that incredible melt factor and mild creaminess
• Sharp cheddar cheese: Adds the perfect sharp contrast to the mild mozzarella
• Baby spinach or arugula: Optional but adds a fresh peppery bite and pretty color

Instructions

Roast the tomatoes low and slow:

Preheat your oven to 300°F and arrange tomato slices on a parchment lined baking sheet. Drizzle with olive oil and season with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until the tomatoes are deeply caramelized and intensified in flavor but still hold their shape. Let them cool slightly while you assemble the rest.

Build your sandwich layers:

Butter one side of each bread slice generously. Place two slices butter side down and spread the unbuttered sides with pesto. Layer on mozzarella, roasted tomatoes, cheddar, and greens if using, then top with remaining bread slices butter side up.

Grill to golden perfection:

Heat a skillet over medium low heat and add the sandwiches. Cook for 4 to 5 minutes per side, pressing gently with your spatula, until the bread is deeply golden and the cheese is completely melted. Slice diagonally and serve while the cheese is still molten.

Save

My teenage son, who usually claims hes too busy for proper meals, walked in while I was making these and actually stopped scrolling on his phone. The smell of roasting tomatoes followed by butter and melting cheese was too much to resist. We ended up eating together at the counter, just the two of us, and he told me it was the best sandwich hed ever had. That moment of connection over something so simple is why I keep coming back to this recipe.

Choosing Your Cheese

Ive learned that the combination of mozzarella and sharp cheddar is pure magic, with the mozzarella providing that incredible stretch and the cheddar cutting through with its bold flavor. Sometimes I swap in fontina when I want something more nutty, or provolone for a smokier note. The key is having one cheese that melts beautifully and another with enough personality to stand up to the roasted tomatoes.

Making It Your Own

This recipe welcomes creativity, and Ive had such fun experimenting over time. Sun dried tomato pesto adds another layer of tomato intensity, while a pinch of red pepper flakes in the regular pesto gives it this gentle warmth that surprises people. For something completely different, try swapping the bread for ciabatta or adding a thin layer of caramelized onions along with the roasted tomatoes.

Perfect Pairings

A simple green salad with bright vinaigrette cuts through all that richness perfectly, or you can go full comfort mode with a cup of tomato soup. I also love serving these with a bowl of hot minestrone on cold days. For drinks, crisp white wine or even an ice cold beer works wonderfully.

• Make extra roasted tomatoes to keep in the fridge for quick additions to pasta or eggs
• If your bread is very thick, reduce the heat to low and give it more time to melt the cheese without burning
• These sandwiches reheat surprisingly well in a 350°F oven for about 10 minutes if you need to make them ahead

Save

There is something so deeply satisfying about taking a classic we all loved as kids and elevating it into something that feels special. This sandwich still has that comfort food soul, but with grown up flavors that make every bite feel like a treat.

Recipe Q&A

→ Why slow-roast the tomatoes first?

Slow-roasting at 300°F concentrates the natural sugars in tomatoes, creating deep caramelized flavors that add sweetness and umami. This prevents the sandwich from becoming watery while intensifying the tomato taste to complement the rich cheeses.

→ What cheese combination works best?

Mozzarella provides excellent melt and stretch, while sharp cheddar adds tangy depth. Provolone offers mild nuttiness, and fontina delivers creamy richness. The blend ensures both perfect melting properties and complex flavor profiles.

→ Can I use store-bought pesto?

Absolutely. Quality store-bought basil pesto works beautifully here. For extra depth, try sun-dried tomato pesto or add red pepper flakes to your pesto layer for subtle heat that cuts through the rich cheeses.

→ Why cook over medium-low heat?

Lower heat allows the bread to toast evenly and become golden while giving the thick cheese layers time to melt completely. High heat burns the bread before the center heats through, leaving you with cold cheese and charred exterior.

→ What bread is ideal for this sandwich?

Rustic sourdough or country bread with substantial structure holds up well to the generous fillings. The bread needs enough heft to support layers of cheese and roasted tomatoes without becoming soggy or falling apart during cooking.

→ How do I prevent the sandwich from getting soggy?

Pat roasted tomatoes gently with paper towels to remove excess moisture before layering. Also, ensure your pesto isn't overly oily—spreading it thin helps maintain structural integrity while still delivering plenty of flavor.