Save The smell of slow-roasting tomatoes filled my entire apartment last Sunday while I procrastinated on actual work. Something about that concentrated sweetness made me abandon productivity and start rooting through the fridge for bread. This sandwich happened entirely by accident, but now its become the thing I make when only serious comfort food will do.
My roommate walked in mid-roast and literally asked what died in the oven because the tomato scent was so intense. But when she took a bite of the first sandwich, she stopped asking questions and started demanding I make another. Theres something about the way the cheeses meld with the sweet tomatoes that makes people forget their manners entirely.
Ingredients
- Large ripe tomatoes: These need to be meaty and flavorful because roasting concentrates their essence so choose ones that give slightly when pressed
- Rustic sourdough bread: The tang and sturdy texture hold up beautifully under all those layers without turning into mush
- Basil pesto: Homemade is lovely but dont stress about it a good jarred pesto works perfectly here
- Mozzarella and sharp cheddar: The mozzarella brings the melt while cheddar punches up the flavor balance is everything
- Unsalted butter: Softened to room temp so it spreads evenly without tearing the bread
- Olive oil and seasonings: Simple enhancements that transform tomatoes into something entirely new
- Baby spinach or arugula: Optional but adds a fresh bright note against all that richness
Instructions
- Roast the tomatoes low and slow:
- Preheat your oven to 300°F and line a baking sheet with parchment paper. Slice tomatoes about a quarter inch thick and arrange them without overlapping. Drizzle with olive oil then sprinkle with sea salt black pepper and dried oregano.
- Let them caramelize:
- Roast for 50 to 60 minutes flipping them halfway through. You want them deeply caramelized but still holding their shape not dried into chips. Let them cool slightly on the pan while you prep everything else.
- Build your foundation:
- Spread softened butter on one side of each bread slice. Lay two slices buttered side down and spread a generous tablespoon of pesto on the upward-facing unbuttered sides.
- Crisp to perfection:
- Heat a skillet or griddle over medium-low heat. Cook sandwiches for 4 to 5 minutes per side pressing gently with your spatula. Youre looking for golden bread and cheese thats molten and threatening to escape.
Save Last winter I made these during a snow day while watching old movies and my neighbor texted asking what smelled so good. She ended up coming over with tomato soup and we ate grilled cheese on the couch while the snow piled up outside. Some recipes are just meant for sharing even when you originally planned to eat alone.
Choosing Your Cheese
Ive tried every cheese combination imaginable and heres what works best. You need one melty cheese like mozzarella fontina or provolone as your base then something assertive like sharp cheddar gruyère or smoked gouda to cut through all that sweetness. The contrast is what makes each bite interesting instead of just one-note rich.
The Tomato Factor
Roma tomatoes work beautifully because theyre meaty but heirlooms add incredible flavor complexity if you can find them. Just avoid watery grocery store tomatoes in winter because roasting wont fix a bland tomato. The season matters more than most recipes admit.
Make It Your Own
Sometimes I swap the pesto for tapenade or add sliced red onion before roasting the tomatoes. A drizzle of balsamic glaze over the finished sandwich creates this sweet acidic finish that wakes everything up. But honestly the classic version became a classic for a reason.
- Try spreading a thin layer of garlic confit inside instead of pesto for something mellow and sweet
- Add fresh basil leaves between the tomato and cheese layers for a garden fresh bite
- Press the sandwich in a panini press if you want that restaurant-style ridged crunch
Save Theres something profoundly satisfying about a sandwich that takes an hour to make but disappears in minutes. Time well spent if you ask me.
Common Recipe Questions
- → How long does it take to roast the tomatoes?
Roast tomato slices at 300°F for 50-60 minutes, flipping halfway through. They're ready when deeply caramelized but still holding their shape. This slow roasting concentrates the flavors and creates a rich, sweet taste.
- → Can I make this sandwich with different cheeses?
Absolutely. While mozzarella and sharp cheddar work beautifully together, try smoked gouda, gruyère, provolone, or fontina for different flavor profiles. Mix and match based on your preference for stronger or milder cheese notes.
- → What's the best bread to use?
Rustic sourdough or country-style bread work best because they're sturdy enough to hold the filling without falling apart, and their texture creates a satisfying crunch when buttered and toasted. Thicker slices also help contain the roasted tomatoes.
- → Can I prepare the roasted tomatoes ahead of time?
Yes, roast the tomatoes up to 2 days in advance and store them in an airtight container in the refrigerator. You can also make them at room temperature. Assemble and grill the sandwiches fresh when ready to eat.
- → How do I prevent the bread from getting too dark while melting the cheese?
Cook over medium-low heat rather than high heat. This gives the cheese time to melt completely while the bread toasts gently to golden brown. Pressing gently on the sandwich helps distribute heat evenly without burning the exterior.
- → What can I add to enhance the flavor?
Try sun-dried tomato pesto instead of basil, add a pinch of red pepper flakes to the pesto for heat, or layer in fresh spinach or peppery arugula leaves. A thin spread of garlic aioli also complements the roasted tomatoes beautifully.