Roasted Tomato Soup with Grilled Cheese

My kitchen window fogs up every time I roast tomatoes now, and I never mind it. There's something about the smell of caramelizing tomato skins mixed with garlic that makes the whole house feel smaller and warmer in the best way. I started making this soup on a particularly gray afternoon when I had too many tomatoes and not enough plans, and it's become the thing I make when I need to feel like I'm taking care of someone, even if that someone is just me. The grilled cheese croutons were a happy accident born from impatience and hunger. Now they're the non-negotiable part.

I made this for my neighbor once after she mentioned offhand that she hadn't had a proper meal in days, just coffee and crackers. She stood at my counter with the bowl cradled in both hands, dunking the croutons and smiling with her eyes closed. She didn't say much, but she came back the next week asking if I had any more of that soup with the little sandwiches in it. That's when I realized this recipe wasn't just mine anymore.

Ingredients

• 1.5 lbs ripe tomatoes, halved: The riper, the better; their natural sugars caramelize in the oven and turn into something almost jammy, so don't worry if they're a little too soft for salads.
• 1 medium onion, quartered: Roasting mellows out the sharpness and gives the soup a subtle sweetness that feels like a secret ingredient.
• 4 garlic cloves, peeled: Whole roasted garlic becomes buttery and mild, nothing like its raw bite, so don't skimp here.
• 2 tbsp olive oil: This helps everything caramelize without burning and adds a whisper of richness to the base.
• 1 tsp salt: Brings out the tomato flavor and balances the sweetness, but taste before adding more at the end.
• ½ tsp black pepper: Just enough to add a gentle warmth without overpowering the tomatoes.
• 1 tsp dried thyme or basil: I lean toward thyme in winter and basil in summer, but either works beautifully with roasted tomatoes.
• 2 cups vegetable broth: This loosens everything into soup territory; I've used chicken broth when that's what I had, and it's just as good.
• 1 tbsp tomato paste: Deepens the tomato flavor and gives the soup a slightly darker, more complex color.
• 1 tsp sugar (optional): If your tomatoes are more tart than sweet, this tiny bit makes all the difference without tasting sugary.
• ½ cup heavy cream or whole milk (optional): Turns the soup silky and luxurious, but I've skipped it plenty of times and still loved the result.
• 4 slices sandwich bread: White, wheat, sourdough, whatever you have works; the butter and cheese are the real stars here.
• 4 oz sharp cheddar cheese: Sharp cheddar gives you that tangy, grown-up grilled cheese flavor that doesn't disappear into the soup.
• 2 tbsp unsalted butter, softened: Softened butter spreads easier and crisps up the bread evenly, no cold chunks tearing the slices.

Instructions

Preheat and Prep:

Set your oven to 400°F and let it fully heat up while you get everything ready. This ensures the tomatoes start roasting immediately and caramelize instead of steaming.

Arrange and Season:

Lay the halved tomatoes cut side up on a baking sheet along with the onion quarters and whole garlic cloves, then drizzle everything with olive oil and sprinkle with salt, pepper, and thyme or basil. The cut side facing up lets the tomatoes concentrate their flavor as they roast.

Roast Until Caramelized:

Roast for 25 to 30 minutes until the tomatoes are soft, slightly shriveled, and have dark golden edges. Don't rush this step; those browned bits are pure flavor.

Simmer the Base:

Scrape everything from the baking sheet, including the sticky juices, into a large pot and add the vegetable broth, tomato paste, and sugar if you're using it. Bring it to a simmer over medium heat and let it bubble gently for 10 minutes, stirring now and then.

Blend Until Silky:

Use an immersion blender right in the pot to puree everything until smooth, or carefully transfer it in batches to a countertop blender. Stir in the cream or milk if you want that velvety richness, then taste and adjust the salt and pepper.

Make the Grilled Cheese:

Butter one side of each bread slice, layer cheese between two slices with the buttered sides facing out, then cook them in a skillet over medium heat for 2 to 3 minutes per side until golden and melty. 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.

Save

One night I served this to my brother, who has always been picky about soup, claiming it's just hot juice. He ate two bowls and pocketed three croutons for the road. The next time I made it, he showed up uninvited with a loaf of bread and a block of cheese, ready to help. That's when I knew this recipe had officially won him over.

Storing and Reheating

The soup keeps beautifully in the fridge for up to five days in an airtight container, and it actually tastes richer after a day or two. Reheat it gently on the stove over low heat, stirring occasionally, and add a splash of broth or water if it's thickened up too much. Never store the grilled cheese croutons in the soup; keep them separate in a sealed bag at room temperature and crisp them up in a skillet or toaster oven before serving. I've frozen the soup in portions plenty of times, and it thaws and reheats without losing its silky texture.

Flavor Variations

A pinch of smoked paprika or a dash of cayenne adds warmth and a hint of smokiness that makes people ask what your secret is. I've swapped the cheddar for mozzarella when I wanted the croutons to be stringy and mild, and Gruyère when I was feeling fancy and wanted something nutty. Fresh basil stirred in at the end or a drizzle of good balsamic vinegar right before serving can lift the whole bowl into something special. Sometimes I'll roast a red bell pepper alongside the tomatoes for a slightly sweeter, more complex flavor.

Making It Your Own

This soup is endlessly adaptable depending on what's in your fridge or what kind of day you're having. For a vegan version, use plant-based butter, dairy-free cheese, and coconut cream or cashew cream instead of heavy cream, and it still comes out luscious. If you don't have an immersion blender, a regular blender works fine, just let the soup cool slightly and blend in batches with the lid vented to avoid steam pressure. Serve it with a simple green salad or some crusty bread on the side for a complete, no-fuss meal.

• Try sprinkling freshly grated Parmesan on top of the soup along with the croutons for an extra layer of savory richness.
• If you have leftover grilled cheese croutons, they make an excellent snack on their own or tossed into a Caesar salad.
• For a lighter version, skip the cream entirely and let the natural sweetness of the roasted tomatoes shine through.

Save

This soup has become my answer to cold evenings, unexpected guests, and days when I just need something warm and uncomplicated. I hope it finds a spot in your rotation too, croutons and all.

Recipe FAQs

→ Can I make this soup ahead of time?

Yes, the soup keeps well refrigerated for up to 4 days. Prepare the grilled cheese croutons fresh before serving for maximum crispness. You can reheat the soup gently over low heat, adding a splash of broth if it thickens too much.

→ What's the best way to get perfectly caramelized tomatoes?

Arrange halved tomatoes cut-side up on the baking sheet and roast at 400°F for 25-30 minutes. The dry heat caramelizes the natural sugars, intensifying the flavor. Don't crowd the pan, as this allows steam to escape and promotes browning.

→ Can I use canned tomatoes instead of fresh?

Yes, use about 2 cans of whole peeled tomatoes (28 oz total). Drain excess liquid and roast them the same way. Canned tomatoes work well but won't caramelize as visibly as fresh ones.

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

Prepare the croutons shortly before serving and top the soup just before eating. If making ahead, store them in an airtight container at room temperature. You can briefly re-toast them in a skillet to refresh their crispness.

→ What cheese works best for the croutons?

Sharp cheddar is classic and melts beautifully, but Gruyère adds elegance, mozzarella provides mild creaminess, and fontina brings a sophisticated flavor. Avoid low-moisture cheeses that don't melt well.

→ Is this suitable for vegan diets?

Absolutely. Substitute plant-based butter, vegan cheese, and coconut or cashew cream for the dairy ingredients. The roasted vegetables provide all the richness and comfort you need.