Roasted Tomato Pesto Grilled Cheese

The smell of slow-roasting tomatoes filling my apartment on a rainy Sunday morning changed everything I thought I knew about grilled cheese. I had been experimenting with oven-dried tomatoes for a pasta dish when I realized how incredibly concentrated and sweet they became—almost like tomato candy. Naturally, my brain went straight to sandwich territory. That first bite, with the tangy roasted tomatoes cutting through the rich melted cheese and fragrant basil pesto, made me abandon regular grilled cheese forever. It's the sandwich that convinced my pesto-skeptical husband that basil and cheese belong together.

I made these for my sister when she was recovering from surgery and couldn't tolerate much food, but this sandwich somehow hit the spot. She texted me three days later asking for the recipe, claiming it was the only thing she actually wanted to eat. There's something about the warmth and comfort of melted cheese paired with those concentrated roasted tomatoes that feels like a hug in sandwich form. Now it's our go-to when life feels overwhelming and we need something deeply satisfying but not fussy.

Ingredients

• 2 large ripe tomatoes, sliced 1/4-inch thick: Choose tomatoes that give slightly when pressed—meaty romas or beefsteaks work beautifully since they hold their shape during roasting
• 1 tbsp olive oil: This helps the tomatoes caramelize and develop those concentrated sweet flavors
• 1/4 tsp sea salt: Essential for drawing out moisture and intensifying the tomato flavor
• 1/4 tsp freshly ground black pepper: Adds a subtle warmth that complements the roasted sweetness
• 1/4 tsp dried oregano: Brings an earthy, Mediterranean note that bridges the tomatoes and pesto
• 4 slices rustic sourdough or country bread: Sturdy bread is crucial here—flimsy slices will get soggy from the juicy tomatoes
• 2 tbsp unsalted butter, softened: Buttering the exterior creates that irresistible golden, crispy crust we all crave
• 2 tbsp basil pesto: Homemade is lovely but store-bought works perfectly—just look for one with good green color
• 4 slices mozzarella cheese: The mild, creamy base that provides that gorgeous cheese pull
• 4 slices sharp cheddar cheese: Adds the necessary tang and depth to balance the mild mozzarella
• Optional handful of baby spinach or arugula: Adds fresh contrast and a hint of peppery bite that cuts through the richness

Instructions

Roast the tomatoes:

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

Build your sandwiches:

Spread softened butter on one side of each bread slice. Place two slices butter-side down and spread pest generously on the facing sides. Layer on mozzarella, your roasted tomatoes, cheddar, and greens if using, then top with remaining bread slices butter-side up.

Grill to golden perfection:

Heat a skillet or griddle over medium-low heat—you want it gentle so the cheese melts before the bread burns. Cook sandwiches for 4 to 5 minutes per side, pressing gently with your spatula, until both sides are golden brown and crisp with cheese oozing out the edges.

Save

This sandwich has become my daughters requested meal after every single soccer tournament. There's something about coming home cold and exhausted, smelling those roasted tomatoes and melting cheese, that feels like the ultimate reward. She recently told me she wants to learn to make them herself, claiming she needs to be prepared for college cravings.

Making Ahead

You can roast the tomatoes up to three days ahead and store them in an airtight container in the refrigerator—they actually develop even more flavor as they sit. Just bring them to room temperature before assembling your sandwiches for the best melting results.

Cheese Questions

The mozzarella and cheddar combination is my go-to ratio for perfect melt and flavor balance, but don't be afraid to experiment. Smoked gouda adds incredible depth, gruyère brings nutty sophistication, and fontina creates the most luxurious, velvety texture you can imagine.

Serving Ideas

While this sandwich is absolutely perfect on its own, a crisp green salad with acidic vinaigrette cuts through the richness beautifully. A steaming cup of tomato soup turns it into the ultimate comfort meal, though honestly, most days I just grab a fork and eat it straight from the cutting board standing in my kitchen.

• Try spreading a thin layer of sun-dried tomato pesto instead of regular basil for double tomato intensity
• A pinch of red pepper flakes mixed into the pesto adds lovely warmth that complements the cheese
• Let the sandwich rest for two minutes after grilling so the cheese sets slightly—this prevents that tragic first-bite cheese slide

Save

There's nothing quite like cutting into a perfectly grilled sandwich and watching the cheese stretch and pull as you separate the halves. Simple, satisfying, and absolutely worth every minute of roasting those tomatoes.

Recipe FAQ

→ How long should I roast the tomatoes?

Roast the tomatoes at 300°F for 50-60 minutes, flipping halfway through. They should be deeply caramelized and concentrated in flavor while still holding their shape.

→ Can I use different types of cheese?

Absolutely. Try smoked gouda, gruyère, provolone, or fontina for different flavor profiles. The combination of a melting cheese with a sharper cheese works best for balance and texture.

→ What's the best bread to use?

Rustic sourdough or country bread work wonderfully because they hold up well to the butter and fillings. The sturdy crumb toasts beautifully while staying soft inside.

→ Can I make this vegetarian?

Yes, this sandwich is naturally vegetarian. All ingredients are plant-based or dairy products. Just verify your pesto is made without anchovies if using store-bought.

→ How do I get the cheese perfectly melted?

Cook on medium-low heat for 4-5 minutes per side, pressing gently with a spatula. This slower cooking ensures the bread toasts evenly while the cheese melts completely before the bread burns.

→ What can I serve alongside this?

Pair with a crisp green salad, fresh tomato soup, or a light arugula salad. The acidity and freshness complement the rich, melted cheese beautifully.