Roasted Tomato Pesto Grilled Cheese

The smell of slow-roasting tomatoes filling my tiny apartment on a rainy Tuesday afternoon is something I still crave. I had an abundance of summer tomatoes that needed using, and what started as an experiment turned into one of those sandwiches that makes you pause mid-bite. Something about the sweetness of concentrated tomatoes cutting through rich, melted cheese just works.

My roommate walked in while I was flipping the second sandwich and immediately demanded the recipe. We stood over the stove, slicing them in half and watching cheese pull apart in strings, eating standing up because waiting for plates seemed like too much effort. That impromptu kitchen dinner became a regular thing whenever tomatoes were in season.

Ingredients

• Ripe tomatoes: Choose ones that give slightly when pressed. They will concentrate in flavor as they roast, transforming into something almost candy-like.
• Rustic sourdough bread: The sturdy texture holds up beautifully to the weight of cheese and tomatoes. A country loaf or artisan sourdough with a good crust is ideal.
• Basil pesto: Homemade is wonderful, but a high-quality store-bought version works perfectly. Look for one with bright green color and fresh aroma.
• Mozzarella and sharp cheddar: The mozzarella provides the gorgeous melt factor while cheddar brings the sharp, tangy contrast that keeps it from being too mild.
• Unsalted butter: Softened to room temperature so it spreads easily without tearing the bread.

Instructions

Roast the tomatoes:

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

Prepare the bread:

Spread softened butter on one side of each bread slice. Lay two slices butter-side down on your work surface, then spread one tablespoon of pesto on the unbuttered side of each.

Layer the fillings:

On each pesto-covered slice, layer two slices of mozzarella, a portion of the roasted tomatoes, two slices of sharp cheddar, and a handful of baby spinach or arugula if you like. Top with the remaining bread slices, buttered side facing up.

Grill to perfection:

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

Serve immediately:

Cut each sandwich in half and serve while the cheese is still hot and gooey. The contrast between the crisp, buttery bread and the soft, sweet tomatoes is best enjoyed right away.

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This recipe became my go-to for Sunday suppers during tomato season. There is something deeply satisfying about taking a classic from childhood and elevating it into something that feels both nostalgic and entirely new at the same time.

Make It Your Own

Sun-dried tomato pesto adds an even deeper concentrated flavor, or try adding a pinch of red pepper flakes to regular pesto for gentle heat. For a different cheese experience, smoked gouda brings a wonderful smokiness while gruyère adds nutty complexity.

Perfect Pairings

A crisp green salad with bright vinaigrette cuts through the richness, and a cup of tomato soup makes this a complete comfort meal. The soup-and-sandwich combo is classic for a reason.

Timing and Planning

You can roast the tomatoes up to two days ahead and store them in the refrigerator. This makes assembly incredibly quick on busy weeknights. The tomatoes also freeze beautifully if you want to roast a big batch during peak tomato season.

• Roasting the tomatoes takes the longest, so start that first.
• Keep the heat moderate when grilling to avoid burning the butter before the cheese melts.
• Let the sandwiches rest for just one minute after cooking to prevent the cheese from running out when you slice.

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Hope this sandwich brings you as many happy kitchen moments as it has brought me. Some of the best meals start with simple ingredients and a little patience.

Recipe FAQs

→ How long does it take to roast the tomatoes?

The tomatoes roast in a 300°F oven for 50–60 minutes, flipping halfway through, until they're deeply caramelized but still hold their shape. This slow roasting concentrates their natural sweetness.

→ Can I use different cheeses?

Absolutely. While mozzarella and sharp cheddar create a perfect balance of melt and flavor, you can substitute provolone, fontina, smoked gouda, or gruyère for different taste profiles.

→ What bread works best?

Rustic sourdough or country bread is ideal because it holds up well to the hearty fillings and creates a satisfying crunch. For a gluten-free version, substitute your favorite gluten-free bread.

→ Can I make this ahead?

You can roast the tomatoes up to 2 days in advance and store them in the refrigerator. The sandwiches are best cooked fresh, but you can assemble them ahead of time and cook when ready to serve.

→ What should I serve with this?

A crisp green salad with vinaigrette cuts through the richness beautifully. A cup of tomato soup makes for the ultimate comforting pairing, especially on chilly days.

→ How do I get the crispiest result?

Cook over medium-low heat for 4–5 minutes per side, pressing gently with a spatula. This allows the bread to golden evenly and the cheese to melt completely without burning.