Roasted Tomato Soup with Grilled Cheese

My daughter used to refuse tomato soup until the afternoon I let her help me roast the tomatoes. She stood on her step stool, watching them blister and caramelize in the oven, and when I blended everything together, she insisted on dunking her grilled cheese right into the pot. Now she asks for this combo every time the weather turns cold, and I always make extra croutons because half of them disappear before the soup even hits the table.

I started making this on Sunday nights when I needed something easy but still special. The smell of roasting tomatoes fills the house in a way that feels like youve been cooking all day, even though most of the work is just waiting. My husband started cutting the grilled cheese into cubes without me asking, and now its his unofficial job every time we make this together.

Ingredients

• Ripe tomatoes: The flavor depends on these, so use the ripest ones you can find; if theyre a little too tart, the sugar will balance them out.
• Onion and garlic: Roasting them alongside the tomatoes mellows their sharpness and adds a gentle sweetness that makes the soup taste like it simmered for hours.
• Olive oil: Coat everything generously so the vegetables caramelize instead of drying out; cheap oil works fine here.
• Vegetable broth: This thins the soup to the right consistency, and if you use a good quality broth, it adds another layer of flavor without much effort.
• Tomato paste: Just a tablespoon deepens the tomato flavor and gives the soup a richer color.
• Heavy cream or milk: Optional, but it turns the soup velvety and tames any leftover acidity; I skip it when I want something lighter.
• Sandwich bread and cheddar cheese: Use sturdy bread that wont fall apart when you cube it, and sharp cheddar gives the croutons a tangy bite that cuts through the sweetness of the soup.
• Butter: Softened butter spreads easily and helps the bread get golden and crispy without burning.

Instructions

Roast the vegetables:

Arrange the halved tomatoes cut side up with the onion and garlic on a baking sheet, drizzle everything with olive oil, and season with salt, pepper, and thyme or basil. Roast at 400°F for 25 to 30 minutes until the tomatoes are soft and the edges are starting to char.

Simmer the soup base:

Transfer the roasted vegetables and all the juices from the pan into a large pot, add the vegetable broth, tomato paste, and sugar if using, then bring it to a simmer over medium heat for about 10 minutes. Stir occasionally and let the flavors meld together.

Blend until smooth:

Use an immersion blender right in the pot, or carefully transfer the soup in batches to a countertop blender, and blend until completely smooth. Stir in the cream or milk if you want it creamier, taste, and adjust the salt and pepper as needed.

Make the grilled cheese sandwiches:

Butter one side of each bread slice, layer the cheese between two slices with the buttered sides facing out, then cook in a skillet over medium heat for 2 to 3 minutes per side until golden and the cheese is melted. Let them cool just enough to handle, then cut into 1 inch cubes.

Serve and enjoy:

Ladle the hot soup into bowls and top each one with a generous handful of grilled cheese croutons. Serve immediately while the croutons are still warm and crispy.

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The first time I served this to friends, I worried it was too simple. But one of them dipped a crouton into the soup, closed her eyes, and said it tasted like being a kid again. That moment reminded me that comfort food doesnt have to be complicated, it just has to feel like home.

How to Store and Reheat

The soup keeps well in the fridge for up to four days in an airtight container, and it actually tastes even better the next day once the flavors have had time to settle. Reheat it gently on the stove over low heat, stirring occasionally, and add a splash of broth or water if it thickens too much. The grilled cheese croutons lose their crunch after a few hours, so I always make them fresh right before serving, but you can store the sandwiches whole in the fridge and crisp them up in a skillet when youre ready.

Substitutions and Variations

If you want to make this vegan, swap the butter for plant based spread, use dairy free cheese for the croutons, and skip the cream or replace it with coconut milk or cashew cream. For a smokier flavor, add a pinch of smoked paprika or a chipotle pepper in the blending step. You can also use Gruyère or mozzarella for the croutons if you want something milder, or mix in fresh basil at the end for a brighter, herbier finish.

Serving Suggestions

This soup is hearty enough to be a meal on its own, especially with the croutons, but it also works beautifully as a starter before roast chicken or pasta. I like to serve it with a simple green salad dressed in lemon vinaigrette to cut through the richness. On colder nights, I pour it into mugs and let everyone dunk their croutons while we sit around the table talking, and it turns dinner into something a little more relaxed and fun.

• Make a double batch of the soup and freeze half for a night when you need comfort in a hurry.
• Try sprinkling fresh herbs like parsley or chives over the top just before serving for a pop of color and freshness.
• If youre feeding a crowd, set out a platter of grilled cheese croutons and let people help themselves.

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This soup has become one of those recipes I make without thinking, the kind that feels like a warm hug on a gray afternoon. I hope it becomes that for you too.

Recipe FAQ

→ Can I make this soup ahead of time?

Yes, the soup base freezes well for up to three months. Prepare it through step 5, cool completely, and store in freezer-safe containers. Reheat gently on the stove, adding broth if needed to reach desired consistency. Prepare grilled cheese croutons fresh before serving for best crispness.

→ What's the best way to avoid lumpy soup?

Use an immersion blender for smooth, lump-free results. If using a countertop blender, work in small batches and never fill more than halfway. Allow soup to cool slightly before blending for safety. Blend until completely smooth, about 2-3 minutes per batch.

→ How do I make the grilled cheese croutons crispy?

Butter both the outside surfaces of the bread thoroughly before grilling. Cook over medium heat until golden brown on each side, roughly 2-3 minutes per side. The key is patient, even cooking. Cut into cubes immediately after cooling for crispness that lasts longer.

→ Can I skip the cream for a lighter version?

Absolutely. The soup is delicious without cream. The roasted tomatoes and vegetable broth create natural richness and body. If you prefer extra creaminess without dairy, substitute with coconut milk, cashew cream, or oat milk for similar results.

→ What cheese works best for the croutons?

Sharp cheddar provides robust flavor and melts beautifully, but gruyère, fontina, or aged gouda offer excellent alternatives. Avoid fresh cheeses like mozzarella di bufala, which won't melt evenly. For milder preference, use mild cheddar or monterey jack.

→ How do I store leftovers?

Store soup in airtight containers in the refrigerator for up to four days. Reheat on the stove over low heat, stirring frequently and adding extra broth if needed. Keep croutons separate in an airtight container for up to two days. Crisp them briefly in a skillet before serving.