Save Pin The rain was tapping against my kitchen window last Tuesday when I decided roasted tomatoes deserved more than just being a side dish. I had a surplus of tomatoes from the farmers market and a fresh loaf of sourdough, so I started slow-roasting them while catching up on a podcast. The whole house filled with this incredible concentrated tomato aroma that made me genuinely excited for lunch. Sometimes the best kitchen experiments happen when you are just trying to use up what is in your produce drawer.
My roommate walked in halfway through the tomato roasting process and literally asked what smelled so incredible. She ended up waiting forty minutes just to try one, and now we make these together almost every weekend. There is something about the combination of slow-roasted tomatoes and pesto that turns a simple sandwich into something you would actually serve to friends.
Ingredients
- 2 large ripe tomatoes: Pick ones that yield slightly when squeezed because underripe tomatoes will not develop that deep caramelized sweetness we want after roasting
- 1 tbsp olive oil: This helps the tomatoes roast evenly and prevents them from drying out in the oven
- 1/4 tsp sea salt: Enhances the natural tomato flavor and helps draw out moisture during roasting
- 1/4 tsp freshly ground black pepper: Adds just enough subtle heat to balance the sweetness
- 1/4 tsp dried oregano: Gives an Italian-inspired earthiness that pairs beautifully with the pesto later
- 4 slices rustic sourdough: A sturdy bread is essential here because flimsy slices will fall apart under the weight of all those toppings
- 2 tbsp unsalted butter: Softened to room temperature so it spreads evenly without tearing the bread
- 2 tbsp basil pesto: Homemade is wonderful but a good quality store-bought version works perfectly fine
- 4 slices mozzarella cheese: Provides that classic cheese pull and mild creamy base
- 4 slices sharp cheddar cheese: The sharpness cuts through the mozzarella and adds the kind of bold flavor we need
- Handful of baby spinach: Completely optional but adds a fresh element and a pop of color
Instructions
- Slow-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 them with olive oil, and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping them halfway through, until they are deeply caramelized and concentrated but still hold their shape.
- Prep the bread:
- Spread softened butter on one side of each bread slice. Place two slices butter-side down on your work surface, then spread a generous tablespoon of pesto on the unbuttered side.
- Layer the fillings:
- Top each pesto-covered slice with two mozzarella slices, a layer of those gorgeous roasted tomatoes, two slices of sharp cheddar, and a handful of spinach if you are using it. Finish with the remaining bread slices, buttered side facing up.
- Grill to perfection:
- Heat a large skillet over medium-low heat and add the sandwiches. Cook for 4 to 5 minutes per side, pressing gently with your spatula, until the bread is golden brown and crisp with cheese completely melted inside.
- Serve immediately:
- Let the sandwiches rest for just one minute before slicing them diagonally. This prevents all that molten cheese from escaping the moment you cut into them.
Save Pin This recipe became my go-to comfort food during a particularly stressful month at work. There was something therapeutic about slowly roasting the tomatoes and then carefully assembling each layer. Now whenever I make them, I am reminded that sometimes the best way to handle a chaotic day is to make something warm and cheesy and take twenty minutes to actually enjoy it.
Choosing Your Cheese
The mozzarella and cheddar combination creates the perfect balance of melt and flavor. Mozzarella delivers that incredible stretch factor everyone loves in a grilled cheese, while sharp cheddar brings the bold, tangy notes that prevent the sandwich from being too mild. If you want to experiment, fontina adds nuttiness, gruyère brings complexity, or smoked gouda introduces a subtle smokiness that plays beautifully with the roasted tomatoes.
Making It Your Own
Sometimes I swap the basil pesto for sun-dried tomato pesto when I want even more concentrated tomato flavor. A pinch of red pepper flakes mixed into the pesto adds gentle warmth that cuts through the richness. During summer, fresh heirloom tomatoes work wonderfully, and in winter I have even used high-quality canned tomatoes with surprising success.
Serving Suggestions
A crisp green salad with a bright vinaigrette helps balance the richness of the sandwich. A cup of tomato soup creates that classic comfort food combination, though this sandwich is substantial enough to stand on its own. For a casual dinner, cut the sandwiches into smaller strips and serve them alongside a simple soup or a light arugula salad dressed with lemon and olive oil.
- The roasted tomatoes can be made a day ahead and stored in the refrigerator
- Leftover sandwiches reheat surprisingly well in a 350°F oven for about 10 minutes
- If making for a crowd, keep finished sandwiches warm in a 200°F oven until ready to serve
Save Pin There is honestly nothing quite like cutting into that first sandwich and watching the cheese stretch across your plate. This is comfort food elevated, exactly the kind of meal that makes you grateful you took the time to cook something real.
Recipe FAQs
- → Can I prepare the roasted tomatoes ahead of time?
Yes, roast the tomatoes up to 2 days in advance. Store them in an airtight container in the refrigerator. Bring to room temperature before assembling your sandwich for easier layering.
- → What's the best bread for this sandwich?
Rustic sourdough or country bread works best due to its sturdy crumb structure and ability to hold the fillings. Thicker slices (about 1/2-inch) prevent sogginess and provide better structural support.
- → How do I prevent the cheese from leaking out while cooking?
Keep your skillet heat at medium-low and press gently on the sandwich while cooking. This helps the cheese melt evenly and stay contained. Avoid extremely high heat, which causes cheese to separate too quickly.
- → Can I make this vegetarian?
This sandwich is already vegetarian. It's packed with roasted tomatoes, pesto, and cheese. For vegan alternatives, use dairy-free butter and plant-based cheese, though cooking times may vary slightly.
- → What cheese combinations work best?
The mozzarella and sharp cheddar pairing offers creamy texture with tangy bite. Other excellent options include smoked gouda for depth, gruyère for nuttiness, or provolone for a slightly sharper flavor profile.
- → How can I add more flavor to this sandwich?
Consider sun-dried tomato pesto for intensity, fresh basil leaves beyond the pesto, a pinch of red pepper flakes for heat, or thinly sliced garlic. Fresh arugula or baby spinach adds peppery freshness and nutrients.