Pin It The smell of slow-roasting tomatoes filling my apartment on a rainy Tuesday afternoon changed how I thought about grilled cheese forever. I had been roasting extra tomatoes from my farmers market haul, just letting them concentrate into these jammy little discs of flavor, when hunger struck and I decided to get experimental. The way that sweetness from the caramelized tomatoes cut through the sharp cheddar and creamy mozzarella was nothing short of revelatory. My roommate walked in asking what smelled so incredible, and we ended up making four more sandwiches that night.
I made these for my sister when she was visiting last fall, fresh off a breakup and needing serious comfort food. She took one bite and literally stopped talking, which is saying something for someone who never stops talking about her day. We sat at the kitchen table watching the rain, dipping sandwich corners into tomato soup, and she said it was the first time she had felt truly okay in weeks. Now she texts me every time she makes them herself.
Ingredients
- 2 large ripe tomatoes, sliced 1/4-inch thick: Choose tomatoes that give slightly when pressed, and slice them evenly so they roast at the same rate
- 1 tbsp olive oil: This helps the tomatoes caramelize and prevents them from drying out in the oven
- 1/4 tsp sea salt: Enhances the natural sweetness as the tomatoes concentrate
- 1/4 tsp freshly ground black pepper: Adds just enough bite to balance all that rich cheese
- 1/4 tsp dried oregano: Earthy and aromatic, this bridges the gap between the tomatoes and Italian-inspired pesto
- 4 slices rustic sourdough or country bread: Hearty bread holds up better to the juicy tomatoes and multiple cheese layers
- 2 tbsp unsalted butter, softened: Spreadable butter is crucial here for even golden browning
- 2 tbsp basil pesto: Homemade is wonderful, but do not stress about it, a good jarred pesto works beautifully
- 4 slices mozzarella cheese: The melty, mild base that lets those roasted tomatoes shine
- 4 slices sharp cheddar cheese: Provides the assertive flavor and slight tang that cuts through the richness
- Handful of baby spinach or arugula: Totally optional, but I love how the peppery greens brighten each bite
Instructions
- Roast the tomatoes until they are jammy and concentrated:
- Preheat your oven to 300°F and line a baking sheet with parchment paper for easy cleanup later. Arrange your tomato slices in a single layer, drizzle them with olive oil, then sprinkle with salt, pepper, and oregano. Let them roast for 50 to 60 minutes, flipping them halfway through, until they are shriveled and deeply caramelized but still intact.
- Build your sandwich foundation:
- Spread softened butter on one side of each bread slice, then place two slices butter-side down on your work surface. Spread a generous tablespoon of pesto on each unbuttered side, layering two slices of mozzarella, a portion of those incredible roasted tomatoes, two slices of cheddar, and some greens if you are using them.
- Grill to golden perfection:
- Top with the remaining bread slices, buttered side facing up, and cook in a large skillet over medium-low heat for 4 to 5 minutes per side. Press down gently with your spatula and flip carefully, watching for that beautiful golden crust and knowing the cheese is fully melted when you see it starting to ooze out the sides.
Pin It This recipe has become my go-to for Sunday suppers when I want something that feels nourishing but not heavy. There is something about the combination of warm, crusty bread and those concentrated tomatoes that just feels like home.
Make It Your Own
Sun-dried tomato pesto adds an even deeper tomato flavor, and sometimes I will add a pinch of red pepper flakes to the pesto for a subtle kick. The beauty of this recipe is how forgiving it is, so do not be afraid to experiment with different cheese combinations until you find your perfect version.
What to Serve Alongside
A crisp green salad with a bright vinaigrette cuts through all that rich cheese perfectly. I also love serving this with a steaming cup of tomato soup for the ultimate comfort meal experience, especially on chilly evenings.
Storage and Make-Ahead Tips
You can roast the tomatoes up to three days ahead and keep them in the refrigerator, which actually makes them even more flavorful. The assembled sandwiches are best eaten immediately while the cheese is still melty and the bread is at its crispest.
- Wrap leftover roasted tomatoes tightly in the refrigerator for up to five days
- Use gluten-free bread if needed without compromising the overall experience
- Reheat any leftover sandwiches in a skillet rather than the microwave to preserve that golden crust
Pin It There is something deeply satisfying about taking a classic from childhood and elevating it into something that feels sophisticated while still delivering that same comfort. I hope this recipe becomes as special in your kitchen as it has become in mine.
Recipe FAQs
- → Can I prepare the roasted tomatoes ahead of time?
Yes, absolutely. Roast the tomatoes up to 2 days in advance and store them in an airtight container in the refrigerator. This makes assembly much quicker when you're ready to make the sandwiches.
- → What's the best way to prevent the cheese from leaking out?
Stack your cheese slices directly against the bread and ensure the roasted tomatoes are cooled before assembling. Cook on medium-low heat rather than high heat, which gives the cheese time to melt without the bread burning. Press gently while cooking to keep ingredients contained.
- → Can I use fresh tomatoes instead of roasting them?
Fresh sliced tomatoes will work in a pinch, but roasting develops a concentrated sweetness and removes excess moisture that can make the sandwich soggy. For the best texture and flavor, stick with the roasting method.
- → What type of pesto works best?
Homemade basil pesto offers the brightest flavor, but quality store-bought versions work wonderfully. Sun-dried tomato pesto adds an interesting twist. Avoid overly chunky pestos that may tear the bread during assembly.
- → How do I make this vegetarian or vegan?
This sandwich is already vegetarian. For a vegan version, substitute dairy butter with vegan butter, replace cheese with cashew or nutritional yeast-based alternatives, and use a vegan pesto without cheese or pine nuts.
- → What bread works best for this sandwich?
Rustic sourdough or country bread are ideal because they're sturdy enough to hold the fillings without tearing. Focaccia, ciabatta, or thick-cut whole grain bread are excellent alternatives. Avoid thin white bread, which may fall apart under the weight.