Save to Pinterest The first time I made roasted tomato pesto grilled cheese was actually a happy accident during a rainy Sunday when I was craving something cozy but wanted to use up some tomatoes that were slightly past their prime. I tossed them in the oven on a whim, and that slow roasting transformation turned them into something completely different and their sweetness balanced perfectly with the sharp cheddar.
My partner walked into the kitchen while these were grilling and actually asked what smelled so incredible the butter toasting into the sourdough combined with that savory tomato aroma filling every corner of our tiny apartment. We ate them standing at the counter too impatient to even bother with plates and I knew this was going into our regular rotation forever.
Ingredients
- 2 large ripe tomatoes sliced 1/4 inch thick: The roasting process concentrates their natural sugars and transforms ordinary tomatoes into something jammy and intense
- 1 tbsp olive oil: Helps the tomatoes caramelize and prevents them from drying out during their long roast
- 1/4 tsp sea salt: Essential for drawing out moisture and intensifying flavor as the tomatoes roast
- 1/4 tsp freshly ground black pepper: Adds a gentle heat that cuts through the richness of the cheese
- 1/4 tsp dried oregano: Brings an earthy Italian note that bridges the tomatoes and pesto beautifully
- 4 slices rustic sourdough or country bread: The sturdy texture holds up to all the layers and develops an incredible crunch when buttered and grilled
- 2 tbsp unsalted butter softened: Creates that golden crispy exterior that makes grilled cheese so addictive
- 2 tbsp basil pesto: Adds fresh herbaceous brightness and another layer of savory depth
- 4 slices mozzarella cheese: Provides the melty gooey foundation that binds everything together
- 4 slices sharp cheddar cheese: Brings the punchy tang that balances the sweet roasted tomatoes perfectly
- Handful of baby spinach or arugula optional: Adds a fresh peppery contrast and makes you feel slightly virtuous about all that cheese
Instructions
- Roast the tomatoes:
- Preheat your oven to 300°F and line a baking sheet with parchment paper then arrange those tomato slices in a single layer before drizzling with olive oil and seasoning with salt pepper and oregano
- Let them get jammy:
- Slide the tomatoes into the oven and roast for 50 to 60 minutes flipping halfway through until theyre deeply caramelized and shriveled but still holding their shape
- Prep your bread:
- While the tomatoes cool slightly spread softened butter on one side of each bread slice getting right to the edges so every bite gets perfectly golden
- Build the layers:
- Place two slices buttered side down on your work surface spread the unbuttered sides with pesto then layer mozzarella roasted tomatoes cheddar and any greens you want
- Grill to perfection:
- Cook the sandwiches in a skillet over medium low heat for 4 to 5 minutes per side pressing gently and watching for that beautiful golden brown crust
- Serve immediately:
- Slice them in half and watch that cheese stretch while the steam escapes carrying the most incredible aroma through your kitchen
Save to Pinterest This grilled cheese has become my go to comfort food whenever life feels overwhelming because the simple act of roasting tomatoes forces me to slow down and be present in the kitchen. Something about that long slow roasting time feels almost meditative and the end result is always worth every minute of patience.
Choosing The Right Bread
I learned the hard way that flimsy sandwich bread turns into a soggy disappointment under all these layers so sturdy sourdough or a dense country loaf is absolutely essential. The bread needs to be substantial enough to hold the weight of melting cheese and roasted tomatoes without collapsing into a messy puddle.
The Cheese Strategy
Using mozzarella as your base provides that incredible stretch while sharp cheddar delivers the bold flavor punch that cuts through the sweetness of the tomatoes. This combination was discovered after many failed experiments using fancy artisan cheeses that tasted delicious but never quite melted the way I wanted.
Make Ahead Magic
Batch roasting tomatoes has become one of my favorite kitchen habits because they keep for days in the refrigerator and transform everything from pasta to morning eggs. Your future self will thank present you when roasted tomatoes are ready and waiting in your fridge.
- Double the tomato roasting portion and store extras in an airtight container with a drizzle of olive oil
- Try swapping in sun dried tomato pesto for an even more intense tomato flavor throughout the sandwich
- A pinch of red pepper flakes mixed into the pesto adds just enough heat to keep things interesting
Save to Pinterest Some recipes are just recipes but this one has become a genuine ritual in my kitchen and I hope it brings you the same simple comfort it has brought me on countless rainy afternoons.
Recipe FAQs
- → Can I make the roasted tomatoes ahead of time?
Absolutely. Roast the tomatoes up to 3 days in advance and store them in an airtight container in the refrigerator. They'll actually develop more flavor as they sit. Bring to room temperature before assembling your sandwich for the best melting results.
- → What type of bread works best for this sandwich?
Rustic sourdough or country bread holds up beautifully to the hearty fillings and grilling process. Look for a sturdy loaf with a good crumb structure that won't get soggy. Ciabatta or a dense whole grain would also work well.
- → Can I use store-bought pesto?
Store-bought pesto works perfectly fine—just look for a brand with fresh ingredients and vibrant color. If you want to elevate it further, stir in a handful of fresh basil leaves or a teaspoon of olive oil to loosen it slightly before spreading.
- → Why roast the tomatoes instead of using fresh?
Roasting concentrates the natural sugars in tomatoes, creating deep, sweet, umami flavors that fresh tomatoes can't match. The slow roasting process removes excess moisture so your sandwich stays crisp rather than becoming soggy.
- → What other cheeses work well in this combination?
Provolone adds mild creaminess, fontina brings nutty richness, and gruyère offers excellent melt with complex flavor. For something different, try smoked gouda for a smoky dimension or Monterey Jack for extra meltiness.
- → How do I get the cheese perfectly melted without burning the bread?
Keep your heat at medium-low and be patient. Lower heat allows the cheese to melt completely while the bread gradually crisps and turns golden. Press gently with your spatula to ensure good contact between the bread and cooking surface.