Roasted Tomato Pesto Grilled Cheese

The first time I made roasted tomato pesto grilled cheese, it was supposed to be a quick lunch but ended up taking three hours because I got obsessed with getting those tomatoes perfectly caramelized. My kitchen smelled like an Italian bistro, and I honestly didn't mind the wait one bit. Now whenever slow-roasted tomatoes are in the oven, that rich, concentrated aroma immediately takes me back to that lazy Sunday afternoon experimenting with what became my ultimate comfort food sandwich.

Last winter, my friend came over for what she thought was a simple grilled cheese lunch and actually asked if I'd secretly taken culinary classes. The way the pesto permeates through the bread while the cheese gets all melty and the tomatoes add this burst of sweetness just hits different. She ended up asking for the recipe before she even finished her first half.

Ingredients

• Ripe tomatoes: Choose tomatoes that give slightly when pressed because they'll concentrate into the most flavorful roasted version of themselves
• Olive oil: Don't be shy with it, the oil helps those tomatoes roast into something almost jammy rather than just dried out
• Rustic bread: Sourdough or country bread has the structure to hold everything together without getting soggy and develops the most beautiful golden crust
• Basil pesto: Whether homemade or store-bought, make sure it's bright green and not too oily for the best flavor distribution
• Mozzarella: This provides that incredible melt factor and mild creaminess that lets the other flavors shine
• Sharp cheddar: The sharpness cuts through the richness and adds that classic grilled cheese tang we all love

Instructions

Roast the tomatoes:

Preheat 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, until deeply caramelized and slightly shriveled but still holding their shape.

Prep the bread:

Spread softened butter on one side of each bread slice and lay two slices butter-side down, then spread 1 tablespoon pesto on each unbuttered side.

Build the sandwiches:

Layer mozzarella, roasted tomatoes, cheddar, and optional greens on the pesto-covered slices, then top with remaining bread slices butter-side up.

Grill to perfection:

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

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My roommate used to tease me about being 'extra' for roasting tomatoes for grilled cheese until she took a bite and literally went silent for a full minute. Now she requests them specifically on grocery day so we can meal-prep a batch together.

Making It Your Own

I've discovered that swapping in sun-dried tomato pesto creates this intense double-tomato situation that's honestly incredible. A pinch of red pepper flakes mixed into the pesto adds just enough warmth to cut through all that cheese without overpowering the delicate roasted tomatoes.

The Bread Choice Matters

After testing probably seven different bread types, thick-cut sourdough remains undefeated. The tang plays beautifully with the pesto and it develops this shatteringly crispy exterior while staying pillowy inside, which is exactly what you want in a grilled cheese experience.

Serving Suggestions

A simple arugula salad with lemon vinaigrette cuts through the richness perfectly. Sometimes I'll serve it alongside tomato soup for the ultimate comfort meal combo, though the sandwich is satisfying enough on its own.

• Let the sandwiches rest for a minute before slicing so the cheese sets slightly
• A sharp knife helps achieve clean cuts without dragging all the cheese out
• Cutting diagonally somehow makes everything taste better

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There's something deeply satisfying about taking that first bite and hearing the crunch, followed immediately by all those layers of flavor. This sandwich has become my go-to when I need food that feels like a hug.

Recipe Questions & Answers

→ Can I use store-bought pesto?

Yes, store-bought basil pesto works perfectly well in this sandwich. Look for a high-quality brand with fresh ingredients for the best flavor.

→ What cheese works best?

The combination of mozzarella for melt and sharp cheddar for flavor is ideal. Provolone, fontina, gruyère, or smoked gouda also make excellent substitutions.

→ Can I roast the tomatoes ahead?

Absolutely. Roast the tomatoes up to 2 days in advance and store them in an airtight container in the refrigerator. They actually develop more flavor over time.

→ How do I get the crispiest bread?

Cook over medium-low heat to allow the cheese to melt completely before the bread burns. Pressing gently with a spatula helps ensure even contact with the pan.

→ Is this freezer-friendly?

While best enjoyed fresh, you can assemble and freeze the uncooked sandwiches. Thaw in the refrigerator before grilling.

→ What can I serve alongside?

A crisp green salad with vinaigrette or a warm cup of tomato soup makes excellent sides. For a heartier meal, add a simple vegetable soup.