Roasted Tomato Pesto Grilled Cheese

The first time I made this, my kitchen smelled like an Italian bistro for hours. Those slow-roasted tomatoes concentrate into something entirely different than fresh ones, almost candy-like and deeply savory. My roommate walked in mid-roast and literally asked what restaurant I'd ordered from, then couldn't believe it was just tomatoes in the oven.

I made these for a rainy Sunday lunch when friends dropped by unexpectedly. They were supposed to be quick grilled cheese, but one bite had everyone putting down their phones and actually talking about food. Now it's the most requested comfort food in my house, especially on dreary days when you need something that hugs you back.

Ingredients

• Large ripe tomatoes: Slice them exactly 1/4 inch thick, thinner and they disappear, thicker and they won't caramelize properly in the oven
• Olive oil: Don't skimp here, the oil helps those tomatoes concentrate into flavor bombs
• Rustic sourdough or country bread: Sturdy bread holds up to the weight of all that cheese and juicy tomatoes without turning mushy
• Unsalted butter: Soften it properly so you can spread it thinly without tearing the bread
• Basil pesto: Homemade is wonderful but a good jarred pesto works perfectly, just don't use the cheap stuff
• Mozzarella cheese: Provolone or fontina work too, you want something that gets wonderfully gooey
• Sharp cheddar cheese: This brings the sharpness that cuts through all that rich cheese and tomato sweetness
• Baby spinach or arugula: Optional but adds a nice fresh bite and makes you feel slightly virtuous

Instructions

Roast the tomatoes low and slow:

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

Prep your bread canvas:

While the tomatoes roast, spread softened butter on one side of each bread slice, getting right into the corners. Lay two slices buttered side down and spread each with about a tablespoon of pesto on the unbuttered side, going almost to the edges.

Layer like you mean it:

Pile on two slices of mozzarella, then arrange those beautiful roasted tomatoes, followed by two slices of sharp cheddar. Add a handful of spinach or arugula if you're using it, then crown with the remaining bread slices, buttered side facing up.

Grill to golden perfection:

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

Slice and serve immediately:

Cut each sandwich in half diagonally and watch that cheese stretch. The roasted tomatoes should be soft and jammy, the pesto aromatic, and the bread perfectly crisp with just enough give.

Save

My daughter now requests this for her birthday dinner instead of cake some years. There's something about the combination of warm bread, melted cheese, and those sweet roasted tomatoes that feels like being wrapped in a blanket on the couch watching movies.

Making It Your Own

Sometimes I swap in sun-dried tomato pesto for an even more intense tomato flavor, or add a pinch of red pepper flakes to the regular pesto for subtle heat. Smoked gouda or gruyère can completely transform the sandwich into something entirely new.

Timing Your Roast

You can roast the tomatoes up to three days ahead and keep them in the fridge. Actually, they develop even more flavor overnight, so this might be the ultimate meal prep secret weapon.

What To Serve Alongside

A crisp green salad with bright vinaigrette cuts through all that richness beautifully. Or go full comfort mode with a cup of tomato soup, though I'll admit that might be tomato overkill for some people.

• Let sandwiches rest for a minute before slicing so the cheese doesn't escape completely
• Cut your roasted tomato slices to fit the bread if they're hanging over the edges
• Keep the heat medium-low, patience is what separates good grilled cheese from great grilled cheese

Save

This sandwich taught me that sometimes the simplest comfort food just needs a little extra attention to become something unforgettable.

Recipe Questions & Answers

→ Why roast the tomatoes first?

Slow-roasting concentrates the natural sugars in tomatoes, creating deep caramelized flavors that add sweetness and umami. This prevents the sandwich from becoming watery while delivering an intense tomato essence that fresh tomatoes can't provide.

→ Can I use different bread?

While rustic sourdough or country bread works best for its structure and flavor, you can use ciabatta, French bread, or even gluten-free alternatives. Just choose hearty slices that can hold the generous fillings without getting soggy.

→ What's the best cheese combination?

The mozzarella provides excellent melt and creaminess while sharp cheddar adds bold flavor punch. You can also try provolone for mild nuttiness, fontina for earthy notes, or gruyère for sophisticated complexity.

→ How do I prevent soggy bread?

The key is roasting tomatoes until they're no longer releasing moisture. Also, butter the exterior thoroughly and cook over medium-low heat to ensure the bread crisps completely before the cheese finishes melting.

→ Can I make this ahead?

You can roast tomatoes up to 3 days in advance and store them in the refrigerator. The sandwiches are best assembled and cooked just before serving, but you can prep all ingredients beforehand for quick assembly.

→ What temperature should I cook at?

Medium-low heat is crucial. Too high and the bread burns before the cheese melts; too low and you'll wait forever. You want gentle, steady heat that creates a golden crust while allowing the interior to warm through completely.