Save My neighbor brought over a jar of homemade pesto the same week I had more tomatoes than I knew what to do with. I was craving something warm and melty but didn't want to spend the afternoon in the kitchen. Tossing those tomatoes in the oven while I answered emails turned out to be the smartest lazy decision I've made. When I finally assembled that first sandwich, the smell alone had me texting her a thank you before I even took a bite. It's been my go-to ever since when I want comfort food that feels a little elevated.
I made this for my sister when she was having a rough week, and she ate it standing over the counter, eyes closed. She told me later it was the first thing that actually tasted good to her in days. We didn't talk much that afternoon, just sat in the kitchen while she finished every crumb. Sometimes a really good sandwich is exactly the right kind of comfort, no words required.
Ingredients
- Ripe tomatoes: You want them firm enough to slice cleanly but ripe enough to smell sweet, roasting concentrates all that flavor into something almost candy like.
- Olive oil: A good drizzle helps the tomatoes caramelize without drying out, don't be stingy here.
- Sea salt and black pepper: Simple seasoning is all you need, the slow roast does the heavy lifting.
- Dried oregano: Adds a subtle earthiness that plays nicely with the pesto later.
- Rustic sourdough or country bread: You need something sturdy with a little chew, flimsy sandwich bread will fall apart under all that cheese.
- Unsalted butter: Softened butter spreads easier and gives you that perfect golden crust.
- Basil pesto: Homemade is gorgeous but a good store bought jar works just fine, taste it first to make sure it's bright and garlicky.
- Mozzarella cheese: Melts like a dream and keeps things creamy, provolone or fontina are excellent swaps.
- Sharp cheddar cheese: Adds a tangy bite that balances the sweet tomatoes beautifully.
- Baby spinach or arugula: Optional but I love the little peppery crunch it adds, plus it makes me feel slightly virtuous.
Instructions
- Prep your oven and tomatoes:
- Preheat to 300°F and line a baking sheet with parchment so nothing sticks. Arrange your tomato slices in a single layer, drizzle with olive oil, and season with salt, pepper, and oregano.
- Roast low and slow:
- Slide the tomatoes into the oven for 50 to 60 minutes, flipping them halfway through so they caramelize evenly. They should look wrinkled and jammy but still hold together when you poke them.
- Butter your bread:
- Spread softened butter on one side of each slice, this is what gives you that gorgeous golden crust. Lay two slices buttered side down on your counter.
- Build the sandwich:
- Spread a tablespoon of pesto on the unbuttered side of each slice, then layer on mozzarella, roasted tomatoes, cheddar, and greens if you're using them. Top with the remaining bread slices, buttered side facing up.
- Grill until golden:
- Heat a skillet over medium low and add your sandwiches, pressing gently with a spatula. Cook 4 to 5 minutes per side until the bread is crispy and the cheese is completely melted and oozy.
- Serve hot:
- Slice in half and eat immediately while the cheese is still stretchy. Patience is not your friend here.
Save The first time I brought these to a potluck, someone asked if I'd gotten them from a café downtown. I just smiled and said I had a good recipe, but honestly it felt incredible to make something that simple taste that special. Food doesn't have to be complicated to feel like a treat, sometimes it just needs a little extra love in the details.
Choosing Your Cheese
I've experimented with nearly every cheese combination I could think of, and here's what I've learned. Mozzarella is non negotiable for that creamy melt, but the second cheese is where you can play. Sharp cheddar adds tang, smoked gouda brings a campfire vibe, and gruyère makes it taste ridiculously fancy. Whatever you pick, make sure one cheese melts smoothly and the other adds flavor punch.
Make Ahead Magic
You can roast a whole batch of tomatoes on Sunday and keep them in the fridge for up to five days. They're incredible on pasta, toast, or grain bowls, so even if you don't make sandwiches right away, you won't regret having them around. I usually double the recipe and store them in a jar covered with a little olive oil, they get even better as they sit.
Serving Suggestions
This sandwich is rich and satisfying on its own, but I love pairing it with something crisp and bright. A simple arugula salad with lemon vinaigrette cuts through the cheese perfectly, or you can go full nostalgic and serve it with a bowl of tomato soup for dipping. If you're feeding a crowd, slice the sandwiches into quarters and serve them as fancy little bites.
- Add a drizzle of balsamic glaze over the tomatoes before closing the sandwich for a sweet tangy kick.
- Try spreading a thin layer of garlic aioli on the bread before adding pesto for extra richness.
- If you have fresh basil on hand, tuck a few leaves inside with the greens for a burst of herby freshness.
Save There's something deeply satisfying about turning a handful of simple ingredients into something this crave worthy. I hope this becomes one of those recipes you reach for whenever you need a little comfort wrapped in crispy, melty, golden perfection.
Common Questions
- → How long does it take to roast the tomatoes?
Roast the tomato slices at 300°F for 50–60 minutes, flipping halfway through. They should be deeply caramelized but still hold their shape. Let them cool slightly before assembling the sandwich.
- → Can I make this ahead of time?
Yes, you can roast the tomatoes several hours in advance and store them in an airtight container. Assemble and cook the sandwich just before serving for the best melted cheese and crispy bread texture.
- → What's the best bread to use?
Rustic sourdough or country bread works beautifully due to its sturdy crumb and tangy flavor. For gluten-free, use a hearty gluten-free bread that won't fall apart when toasted.
- → Can I substitute the cheese?
Absolutely. Try smoked gouda, gruyère, provolone, or fontina for different flavor profiles. The key is using cheeses that melt well and complement the pesto and roasted tomatoes.
- → What temperature should the skillet be?
Cook over medium-low heat to ensure the cheese melts completely before the bread burns. This typically takes 4–5 minutes per side. Press gently with a spatula for even cooking and cheese distribution.
- → Is this sandwich vegetarian?
Yes, this is a fully vegetarian sandwich. It contains cheese, butter, bread, tomatoes, pesto, and optional greens. Always check pesto ingredients for anchovies if strict vegetarian.