Pin It Rainy Sunday afternoons were made for sandwiches like this. I stumbled on the roasted tomato trick completely by accident when I had too many garden tomatoes and zero motivation to make sauce. Now the house fills with this incredible slow-roasted aroma that makes everyone wander into the kitchen, asking what smells so good.
My roommate walked in while I was flipping those tomatoes halfway through roasting. She stood there watching me arrange everything so deliberately, then admitted she had never thought about putting this much care into a sandwich. But when she took that first bite, tomato juice running down her wrist, she completely understood.
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Ingredients
- 2 large ripe tomatoes: Roma varieties work beautifully here since they are meaty and not too watery
- 1 tbsp olive oil: Coats the tomatoes for that gorgeous caramelized finish
- 1/4 tsp sea salt: Enhances natural sweetness as the tomatoes concentrate
- 1/4 tsp freshly ground black pepper: Adds just enough warmth against the rich cheese
- 1/4 tsp dried oregano: Brings an Italian note that plays nicely with the pesto
- 4 slices rustic sourdough or country bread: Sturdy enough to hold everything together without getting soggy
- 2 tbsp unsalted butter: Get this soft so it spreads like a dream
- 2 tbsp basil pesto: Homemade is lovely but store-bought absolutely works in a pinch
- 4 slices mozzarella cheese: That classic melt that stretches beautifully
- 4 slices sharp cheddar cheese: Adds the punch that balances the mild mozzarella
- Handful of baby spinach or arugula: Optional but I love the fresh bite against everything warm
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Instructions
- Roast the tomatoes:
- Preheat oven to 300°F and line a baking sheet with parchment. Arrange tomato slices, drizzle with oil, then sprinkle with salt, pepper, and oregano. Roast 50 to 60 minutes, flipping halfway, until deeply caramelized but still holding their shape.
- Prep the bread:
- Spread softened butter on one side of each bread slice. Place two slices buttered side down on your work surface and spread pesto generously on the unbuttered sides.
- Build the sandwich:
- Layer on mozzarella, roasted tomatoes, cheddar, and greens if using. Top with remaining bread slices, buttered side facing up, pressing down slightly to help everything settle.
- Grill to perfection:
- Cook in a skillet over medium-low heat for 4 to 5 minutes per side. Press gently and flip when golden brown, then cook until cheese is completely melted and the second side is beautifully crisp.
Pin It This sandwich turned a random Tuesday dinner into something my kids still talk about months later. Nothing beats that moment when you cut it diagonally and the cheese just pulls apart in the most gorgeous way possible.
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Choosing Your Cheese
Provolone or fontina instead of mozzarella works wonderfully if you want something nuttier. Gruyère adds sophistication while smoked gouda brings this incredible depth that pairs unexpectedly well with the roasted tomatoes.
Getting That Golden Crust
Butter needs to be soft enough to spread without tearing the bread. Some people swear by mayonnaise instead of butter for an even crispier exterior, and honestly, they might be onto something worth trying.
Serving Suggestions
A simple green salad with bright vinaigrette cuts through all that richness beautifully. Or go all in and serve alongside tomato soup for the ultimate comfort meal experience.
- Sun-dried tomato pesto adds another layer of concentrated flavor
- A pinch of red pepper flakes in the pesto brings gentle heat
- Let the sandwiches rest a minute before slicing so the cheese sets slightly
Pin It Some days you just need grilled cheese that feels like a warm hug. This is that sandwich, every single time.
Recipe FAQs
- → Can I use store-bought pesto?
Yes, store-bought basil pesto works perfectly well in this sandwich. Choose a high-quality brand with fresh ingredients for the best flavor. You can also substitute sun-dried tomato pesto for an extra layer of tomato intensity.
- → Why roast the tomatoes first?
Roasting concentrates the tomato flavor and removes excess moisture, preventing your sandwich from becoming soggy. The slow roasting process also creates natural sweetness and caramelization that complements the rich cheese and aromatic pesto.
- → What other cheeses work well?
While mozzarella and sharp cheddar create an excellent melt and flavor balance, you can experiment with provolone, fontina, gruyère, or smoked gouda. Each brings its own character to the sandwich.
- → Can I make this gluten-free?
Absolutely. Simply substitute your favorite gluten-free bread for the sourdough. Ensure your pesto is also gluten-free, as some brands may include thickeners or additives containing gluten.
- → How do I prevent the bread from burning before the cheese melts?
Cook over medium-low heat and be patient. Lower heat allows the bread to toast gradually while giving the cheese enough time to melt completely. Pressing gently with a spatula helps ensure even contact with the pan.
- → Can I add other ingredients?
Yes, baby spinach or arugula adds fresh contrast. You could also include caramelized onions, sliced avocado, or a swipe of balsamic glaze for extra depth.
