Roasted Tomato Pesto Grilled Cheese

A gourmet twist on the classic grilled cheese, this sandwich brings together the slow-roasted sweetness of tomatoes with the vibrant punch of basil pesto. It is a comforting yet sophisticated dish that elevates a simple lunch into a restaurant-quality experience.

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By layering the cheeses around the roasted tomatoes and pesto, you create a melty barrier that keeps the bread perfectly toasted and ensures every bite is gooey and flavorful.

Ingredients

• Roasted Tomatoes: 2 large ripe tomatoes (sliced 1/4-inch thick), 1 tbsp olive oil, 1/4 tsp sea salt, 1/4 tsp freshly ground black pepper, 1/4 tsp dried oregano.
• Sandwich: 4 slices rustic sourdough or country bread, 2 tbsp unsalted butter (softened), 2 tbsp basil pesto (homemade or store-bought), 4 slices mozzarella cheese (or provolone or fontina), 4 slices sharp cheddar cheese, baby spinach or arugula leaves (optional).

Quickly chop vegetables, blend sauces, and prepare dips or dressings for fast, everyday meal prep.

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Instructions

Step 1

Preheat oven to 300°F (150°C). Line a baking sheet with parchment paper.

Step 2

Arrange tomato slices on the prepared baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, until tomatoes are deeply caramelized but still hold their shape. Let cool slightly.

Step 3

Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface.

Step 4

Spread 1 tbsp pesto on each unbuttered side. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Cover with remaining bread slices, buttered side up.

Step 5

Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4–5 minutes per side, pressing gently, until golden brown and cheese is fully melted.

Step 6

Slice in half and serve immediately.

Zusatztipps für die Zubereitung

Low and slow is the key to both stages of this recipe. Roasting the tomatoes at 300°F prevents them from burning while intensifying their flavor, and cooking the sandwich over medium-low heat ensures the thick slices of cheese melt completely without burning the sourdough.

Varianten und Anpassungen

For extra flavor, use sun-dried tomato pesto or add a pinch of red pepper flakes to the pesto. You can also try smoked gouda or gruyère for a different cheese profile, or substitute gluten-free bread to make this recipe gluten-free.

Serviervorschläge

This sandwich pairs exceptionally well with a crisp green salad tossed in a light vinaigrette or a warm cup of creamy tomato soup for the ultimate comfort meal.

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With its golden crust and vibrant layers, this Roasted Tomato Pesto Grilled Cheese is a vegetarian-friendly staple that feels like a special occasion meal every time it's served.

Keeps spoons and utensils off counters while cooking, catching drips and keeping your stovetop clean.

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Recipe FAQs

→ Can I use fresh tomatoes instead of roasted?

Fresh tomatoes will work but lack the deep caramelized flavor that slow-roasting develops. For best results, follow the roasting method. If short on time, use quality sun-dried tomatoes which offer similar intensity.

→ What bread works best for this sandwich?

Rustic sourdough or country bread are ideal because they're sturdy enough to hold melted cheese and roasted tomatoes without falling apart. Avoid thin sandwich bread. Gluten-free varieties work well as substitutes.

→ How do I prevent the cheese from leaking out?

Start with a medium-low heat setting to allow cheese time to melt before the bread browns. Pressing gently while cooking helps seal the filling. Ensuring bread slices are fully buttered on outer sides also prevents leakage.

→ Can this be made ahead and reheated?

Assemble the sandwich ahead, but cook just before serving for optimal cheese melt and bread texture. Reheating previously cooked sandwiches in a skillet on low heat works, though the result won't match fresh preparation.

→ What cheese alternatives work well here?

Smoked gouda, gruyère, fontina, and provolone all pair beautifully with roasted tomatoes and pesto. Combining one sharp cheese with one mild cheese balances flavors. Avoid highly processed slices for better melting quality.

→ How can I customize the pesto flavor?

Use sun-dried tomato pesto for extra depth, or add red pepper flakes to standard basil pesto for heat. Homemade pesto offers more control over ingredients and intensity compared to store-bought versions.