Roasted Tomato Soup with Grilled Cheese

The oven door swung open and the smell hit me first: sweet, jammy tomatoes with little burnt edges that smelled like summer trapped in winter. I was trying to impress no one in particular, just myself really, and I had this idea that roasting tomatoes instead of opening a can might actually change everything. It did. The soup turned out silky and deep, and those little grilled cheese cubes I tossed on top disappeared so fast I had to make another batch before anyone even sat down.

I made this on a drizzly Saturday when my niece came over with a cold and wanted something warm. She is picky, the kind of kid who inspects every spoonful, but she dunked those cheesy croutons into the soup without a word and finished two bowls. Her mom asked for the recipe on the spot. That is when I knew this one was a keeper, not because it was complicated, but because it made someone feel better without trying too hard.

Ingredients

• Ripe tomatoes: The riper, the better. I learned that pale, hard tomatoes will roast forever and never get sweet, so wait for the ones that smell like something when you pick them up.
• Onion and garlic: These roast alongside the tomatoes and turn mellow and golden, adding a base layer of flavor that you cannot skip.
• Olive oil: Use enough to coat everything lightly. It helps with caramelization and keeps anything from sticking or drying out in the oven.
• Dried thyme or basil: I usually go with thyme because it has this earthy, cozy thing going on, but basil works if you want it a little brighter.
• Vegetable broth: This loosens the soup and adds body. Homemade is great, but store-bought works perfectly fine here.
• Tomato paste: Just a tablespoon deepens the tomato flavor and gives the soup a richer color.
• Sugar: Optional, but if your tomatoes are on the tart side, a pinch balances everything out without making it taste sweet.
• Heavy cream or milk: Stir this in at the end for a velvety finish, or skip it entirely if you prefer a lighter, brighter soup.
• Sandwich bread: Soft white bread works best for the croutons because it crisps up fast and holds the cheese without falling apart.
• Sharp cheddar cheese: The sharpness cuts through the richness of the soup. I have also used Gruyere when I am feeling fancy.
• Unsalted butter: Softened butter spreads easily and gives the bread that perfect golden crust in the skillet.

Instructions

Roast the vegetables:

Preheat your oven to 400°F and spread the halved tomatoes, onion quarters, and garlic cloves on a baking sheet. Drizzle everything with olive oil, season with salt, pepper, and thyme, then roast for 25 to 30 minutes until the tomatoes collapse and the edges start to caramelize.

Simmer the soup base:

Scrape all the roasted vegetables and their juices into a large pot, add the vegetable broth, tomato paste, and sugar if using. Let it simmer over medium heat for about 10 minutes, stirring now and then so nothing sticks to the bottom.

Blend until smooth:

Use an immersion blender right in the pot, or carefully transfer the soup in batches to a countertop blender. Blend until it is completely smooth and velvety, then stir in the cream or milk if you want it richer.

Make the grilled cheese croutons:

Butter one side of each bread slice, layer cheese between two slices with the buttered sides facing out, then cook in a skillet over medium heat until both sides are golden and the cheese melts, about 2 to 3 minutes per side. Let them cool just enough to handle, then cut into bite-sized cubes.

Serve hot:

Ladle the soup into bowls and pile the grilled cheese croutons on top. Serve immediately while everything is warm and the croutons are still a little crispy.

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There was this one night when I served this soup to friends who did not usually get excited about vegetarian food. They kept reaching for more croutons, dipping them slowly, letting the cheese stretch between the bowl and their spoon. One of them said it tasted like the best version of childhood, which is maybe the highest compliment a bowl of soup can get. It is funny how something this simple can make people feel like they are home, even if they are just sitting at your table.

Making It Ahead

The soup keeps beautifully in the fridge for up to four days, and honestly it tastes even better the next day after the flavors settle in. I usually make a big batch on Sunday and reheat it throughout the week, adding the cream right before serving so it stays fresh. The grilled cheese croutons are best made fresh, but you can prep the sandwiches in advance and cook them right before you eat. I have also frozen the soup in portions, which works perfectly as long as you leave out the cream and stir it in after reheating.

Serving Suggestions

This soup does not need much to feel like a full meal, but I like to serve it with a simple green salad dressed with lemon and olive oil to cut through the richness. Sometimes I add a handful of fresh basil on top, torn at the last second, which makes it smell like summer even in the middle of February. If you are feeding kids, let them build their own bowls with the croutons on the side. They love the control, and it keeps them from complaining that the soup is too hot or too tomatoey or whatever else they decide that day.

Customizing the Flavor

Once you get the base down, this soup becomes a template you can play with depending on what is in your pantry or what mood you are in. I have stirred in a pinch of smoked paprika for a smoky depth, swapped the thyme for fresh basil at the end, and even added a splash of balsamic vinegar for a little tang. The grilled cheese croutons are fun to experiment with too: mozzarella makes them extra stretchy, Gruyere adds a nutty richness, and pepper jack gives a spicy kick that works surprisingly well.

• Try roasting a red bell pepper alongside the tomatoes for a slightly sweet, smoky twist.
• Add a handful of spinach or kale right before blending if you want to sneak in some greens without changing the flavor too much.
• For a vegan version, use plant-based butter, cheese, and cream, and the soup still turns out creamy and satisfying.

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This is the kind of soup that makes you want to stay in your pajamas all day, the kind that turns a regular Tuesday into something worth slowing down for. I hope it does the same for you.

Recipe Help & FAQs

→ Can I make this soup ahead of time?

Yes, the roasted tomato base stores well in the refrigerator for up to three days. Reheat gently on the stovetop before serving. Make croutons fresh for best crispness, though they can be prepared a few hours ahead and warmed briefly before plating.

→ What's the best way to blend the soup smoothly?

An immersion blender works best for achieving a silky texture directly in the pot. If using a countertop blender, work in batches and never fill more than halfway to avoid splashing. Blend until completely smooth for a velvety consistency.

→ How do I prevent the grilled cheese from burning?

Use medium heat rather than high—this allows the cheese to melt fully while the bread toasts evenly. Butter the outside generously and watch carefully. If edges brown too quickly, lower heat slightly and extend cooking time by a minute or two per side.

→ Can I substitute the cream in the soup?

Absolutely. Whole milk, Greek yogurt, or plant-based alternatives like oat or cashew cream work well. Coconut milk adds richness too. Adjust quantity based on desired creaminess—start with half a cup and add more as needed.

→ What cheese works best for the croutons?

Sharp cheddar is classic and melts beautifully, but Gruyère adds nuttiness, mozzarella offers mild creaminess, and aged gouda brings smoky depth. Choose based on flavor preference, ensuring your cheese melts well at medium heat.

→ How do I make this more flavorful?

Add smoked paprika, a pinch of cayenne, or fresh basil to the roasting vegetables. A splash of balsamic vinegar or lemon juice brightens acidity. For depth, stir in tomato paste or a touch of white wine before simmering.