Roasted Tomato Pesto Grilled Cheese

The first time I slow-roasted tomatoes for this sandwich, my entire apartment smelled like an Italian grandmother's kitchen. I'd planned a quick lunch but ended up waiting an hour, watching those tomato slices transform into jammy, concentrated bites of sunshine. The impatience was real, but that first bite made every minute worth it. Now I keep roasted tomatoes in my fridge just for moments like this.

My roommate wandered in during the roasting phase, drawn by that incredible aroma, and ended up staying for lunch. We ate them standing at the counter, too eager to bother with plates, burning our fingers on the molten cheese but not caring one bit. That afternoon turned into a ritual, and now whenever I make these, I think of tomato-stained counters and the best kind of company.

Ingredients

• 2 large ripe tomatoes: Slice them exactly 1/4 inch thick, thinner and they'll disappear, thicker and they won't roast evenly
• 1 tbsp olive oil: This helps the tomatoes caramelize and prevents sticking
• 1/4 tsp sea salt: Essential for drawing out moisture and concentrating flavor
• 1/4 tsp freshly ground black pepper: Freshly ground makes a noticeable difference here
• 1/4 tsp dried oregano: Adds that Mediterranean note that bridges tomato and cheese
• 4 slices rustic sourdough: The sturdy texture holds up to all these layers without getting soggy
• 2 tbsp unsalted butter: Softened to room temperature for even spreading
• 2 tbsp basil pesto: Homemade is lovely but quality store-bought works perfectly
• 4 slices mozzarella cheese: The melt factor that holds everything together
• 4 slices sharp cheddar cheese: Brings the bold flavor punch
• Handful of baby spinach or arugula: Optional but adds a fresh contrast to all that richness

Instructions

Roast the tomatoes:

Preheat oven to 300°F and arrange tomato slices on a parchment-lined baking sheet, drizzling with olive oil and seasoning with salt, pepper, and oregano. Roast 50 to 60 minutes, flipping halfway, until deeply caramelized and slightly shriveled but still holding their shape.

Build your sandwiches:

Spread butter on one side of each bread slice, then place two slices butter-side down and spread the opposite sides with pesto. Layer mozzarella, roasted tomatoes, cheddar, and greens if using, then top with remaining bread slices butter-side up.

Grill to perfection:

Cook sandwiches in a skillet over medium-low heat for 4 to 5 minutes per side, pressing gently with your spatula, until golden brown and cheese is completely melted.

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This sandwich became my go-to comfort food during a particularly cold winter, the kind where you need something warm and substantial to feel human again. I'd make a batch of roasted tomatoes on Sunday and treat myself to these sandwiches all week long, each bite feeling like a tiny vacation somewhere warmer.

Making It Your Own

Sun-dried tomato pesto creates an even more intense tomato flavor profile, while a pinch of red pepper flakes in the pesto adds gentle heat that cuts through the cheese. Sometimes I'll swap in smoked gouda for the mozzarella when I want that extra smoky depth.

Bread Wisdom

The bread you choose makes or breaks this sandwich. Sourdough's tang works beautifully with pesto, but a sturdy country loaf or ciabatta can be equally delicious. Just avoid soft sandwich bread that'll turn to mush under all these hearty ingredients.

What To Serve Alongside

A crisp green salad with bright vinaigrette cuts through the richness perfectly, while a cup of tomato soup makes this feel like an elevated classic combo. I've also served it alongside a simple bowl of roasted vegetable soup when I want something lighter.

• Let the sandwiches rest 2 minutes before slicing so the cheese sets slightly
• Cut diagonally for that classic diner look that somehow makes everything taste better
• Leftover roasted tomatoes keep for 5 days in the refrigerator

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There's something profoundly satisfying about taking a childhood favorite and elevating it into something that still feels familiar but tastes extraordinary. This sandwich is proof that sometimes the best innovations come from slowing down and paying attention to simple ingredients.

Recipe Questions

→ Can I make the roasted tomatoes ahead of time?

Absolutely! Roast the tomatoes up to 3 days in advance and store them in an airtight container in the refrigerator. They'll actually develop more flavor as they sit. Bring them to room temperature before assembling your sandwiches for the best melting results.

→ What type of bread works best for this sandwich?

Rustic sourdough or country bread is ideal because their sturdy texture holds up well to the generous fillings and creates excellent crunch when grilled. Look for slices that are at least 1/2-inch thick. Ciabatta or a hearty whole-grain bread also work beautifully.

→ Can I use different cheeses?

Definitely! The mozzarella provides excellent melt while cheddar adds sharpness. You can substitute provolone for mozzarella, fontina for extra creaminess, or experiment with Gruyère and smoked gouda for a more sophisticated flavor profile. Just aim for about 4 slices total per sandwich.

→ How do I prevent the bread from burning before the cheese melts?

Cook over medium-low heat and be patient—this takes about 4-5 minutes per side. The gentle heat allows the cheese to melt completely while the bread gradually turns golden. You can also cover the pan for the first few minutes to trap heat and help the cheese melt faster.

→ Is there a faster way to make the tomatoes?

If you're short on time, you can skip roasting and use sun-dried tomatoes packed in oil (drain them well) or slice fresh tomatoes thinly and pat them dry with paper towels to remove excess moisture before assembling. However, the slow-roasted version delivers unmatched sweetness and depth.

→ Can I make this sandwich vegan?

Yes! Use vegan butter or olive oil instead of regular butter, choose a vegan pesto (many contain Parmesan), and substitute your favorite vegan cheese slices. Nut-based cheeses or those made from coconut oil tend to melt well. The roasted tomatoes remain the same and provide plenty of umami flavor.