Roasted Tomato Soup with Grilled Cheese

My kitchen smelled like a pizzeria one rainy October afternoon, and I wasn't even making pizza. I'd tossed halved tomatoes onto a sheet pan with garlic and onion, cranked the oven, and wandered off to fold laundry. When I came back, the tomatoes had collapsed into themselves, their edges dark and sweet, and the whole house felt warmer. I blended them into soup, then pan-fried little grilled cheese sandwiches and cut them into cubes on a whim. My daughter dipped one into her bowl, grinned, and asked if we could eat like this every week.

I made this for a neighbor who'd just had surgery, and she later told me it was the first thing that tasted like home in weeks. I'd tucked the croutons in a separate container so they'd stay crispy, and she said she ate them one by one between spoonfuls, savoring the contrast. That's when I realized this wasn't just soup. It was a small act of care that happened to involve melted cheese and a blender.

Ingredients

• Ripe tomatoes: Use the ripest you can find, even if they're a little bruised, because roasting forgives imperfections and concentrates their sweetness.
• Onion and garlic: Roasting them whole softens their bite and adds a mellow, almost nutty backbone to the soup.
• Olive oil: A good drizzle helps everything caramelize and keeps the vegetables from sticking or drying out.
• Dried thyme or basil: I prefer thyme for its earthy warmth, but basil brings a brighter, more summery note.
• Vegetable broth: Homemade is lovely, but a quality store bought broth works beautifully and saves time.
• Tomato paste: Just a spoonful deepens the tomato flavor and gives the soup a richer color.
• Sugar: A tiny bit balances any acidity, especially if your tomatoes are on the tart side.
• Heavy cream or whole milk: This is optional, but it turns the soup silky and takes the edge off the brightness.
• Sandwich bread: Use sturdy white or sourdough, nothing too soft or it will fall apart in the pan.
• Sharp cheddar cheese: The sharper the better, it stands up to the richness of the butter and contrasts beautifully with the sweet soup.
• Unsalted butter: Softened butter spreads easily and ensures even browning on the bread.

Instructions

Preheat and prep:

Set your oven to 400°F and line a baking sheet with parchment if you want easier cleanup. Halve the tomatoes and arrange them cut side up so they roast evenly and don't steam.

Season and roast:

Toss the tomatoes, onion, and garlic with olive oil, salt, pepper, and thyme, then roast for 25 to 30 minutes until the edges are dark and the juices have thickened. The caramelization is where all the magic happens.

Simmer the soup base:

Scrape everything into a pot, add broth, tomato paste, and a pinch of sugar if needed. Let it bubble gently for 10 minutes so the flavors can marry.

Blend until smooth:

Use an immersion blender right in the pot, or work in batches with a countertop blender, being careful with the hot liquid. Stir in cream or milk at the end if you want that velvety finish.

Make the croutons:

Butter the outsides of your bread, tuck cheese in between, and grill in a hot skillet until golden and crispy, about 2 to 3 minutes per side. Let them cool just enough to handle, then cut into little cubes.

Serve warm:

Ladle the soup into bowls and scatter the grilled cheese croutons on top. They'll stay crispy for a few minutes, then start to soften into the soup, which is equally delicious.

Save

One Sunday, my son asked if he could help make lunch, and I handed him the job of cutting the grilled cheese into cubes. He arranged them in a spiral on top of each bowl, proud as anything, and we ate slowly at the table instead of in front of the TV. That's the kind of meal this is. It slows you down just enough to notice who you're sharing it with.

Storing and Reheating

The soup keeps in the fridge for up to four days in an airtight container, and it reheats beautifully on the stovetop over low heat. I don't recommend freezing it if you've added cream, as it can separate, but the base without dairy freezes well for up to three months. Make fresh croutons each time you serve it, they're quick and worth the extra few minutes.

Swaps and Variations

If you want a smokier flavor, add a pinch of smoked paprika or a chipotle pepper in adobo before blending. For a lighter version, skip the cream and stir in a spoonful of Greek yogurt at the end instead. Mozzarella or Gruyère make wonderful croutons if you're feeling fancy, and sourdough bread adds a pleasant tang. You can even make this vegan by using plant based butter, cheese, and cream, I've done it for friends and no one missed the dairy.

Serving Suggestions

This soup is hearty enough to be the main event with a crisp green salad on the side, or serve it in smaller portions as a starter before roast chicken or pasta. I've brought it to potlucks in a slow cooker with the croutons in a basket alongside, and it always disappears first. On cold nights, I like to pair it with a glass of something red and a thick slice of buttered bread.

• Top with fresh basil or a drizzle of good olive oil for a restaurant style finish.
• Double the crouton recipe, because people will want seconds and they go fast.
• If you have leftover soup, thin it with a bit more broth and toss with cooked pasta for a quick baked dish.

Save

This soup has become my answer to gray days, unexpected guests, and weeks when I need something that feels like a hug in a bowl. I hope it does the same for you.

Recipe FAQs

→ Can I make this soup ahead of time?

Yes, the roasted tomato soup stores beautifully in the refrigerator for up to 4 days or frozen for 3 months. Prepare the grilled cheese croutons fresh before serving for optimal crispness, or store them in an airtight container for 2 days and warm gently in the oven.

→ What's the best way to achieve a smooth, creamy texture?

An immersion blender gives you direct control over texture while keeping everything in the pot. If using a countertop blender, work in batches and be careful with hot liquid. Blend longer for silkier results. The optional cream or milk adds richness, but the soup is naturally creamy from roasted tomatoes.

→ How do I prevent the grilled cheese croutons from getting soggy?

Cook and cube the grilled cheese sandwiches just before serving. The warm soup's heat will soften them slightly, but serving immediately maintains crispness. For a sturdier crouton, cool completely before cubing and add just before eating.

→ What cheese works best for the croutons?

Sharp cheddar provides classic flavor and melts beautifully. Gruyère offers nutty depth, while mozzarella keeps things mild. Avoid soft cheeses that melt unevenly. For dairy-free versions, use quality plant-based cheese that melts well.

→ Can I adjust the soup's acidity?

Roasting tomatoes naturally concentrates their sweetness, but fresh tomatoes vary in acidity. Add a pinch of sugar to balance tartness, or stir in a touch of balsamic vinegar for complexity. Taste as you blend and adjust seasonings gradually.

→ How do I make this suitable for dietary restrictions?

The soup base is naturally vegetarian and can be vegan using vegetable broth and omitting dairy. For dairy-free versions, substitute plant-based butter, cheese, and cream alternatives in equal amounts. Use gluten-free bread for the croutons if needed.