Roasted Tomato Soup with Grilled Cheese

The smell of caramelized tomatoes hit me before I even opened the oven door. I was testing this recipe on a rainy Tuesday, hoping to use up a pile of tomatoes that were teetering on the edge of too ripe. What came out was something I never expected: a soup so sweet and concentrated it tasted like summer distilled into a bowl. The grilled cheese croutons were a last-minute idea born from leftover sandwich bread, and now I can't imagine the soup without them.

I served this to my neighbor's kids one evening when their mom was working late. They were skeptical at first, poking at the orange bowl with suspicion. Then one of them dunked a grilled cheese cube into the soup, and suddenly everyone wanted seconds. That night taught me that comfort food doesn't need to be complicated, it just needs to feel like a hug in a bowl.

Ingredients

• Ripe tomatoes: The backbone of this soup, choose tomatoes that are heavy and fragrant, even if they're a little soft, roasting will concentrate their sweetness.
• Onion and garlic: Roasting them alongside the tomatoes adds a mellow, caramelized depth that raw alliums simply can't provide.
• Olive oil: A good drizzle helps the vegetables char and caramelize without drying out, bringing out their natural sugars.
• Dried thyme or basil: Either herb works beautifully, thyme adds earthiness while basil brings a hint of sweetness that pairs perfectly with tomatoes.
• Vegetable broth: This loosens the roasted vegetables into a silky soup, use low-sodium if you want full control over the salt level.
• Tomato paste: A spoonful deepens the color and amplifies the tomato flavor, think of it as turning up the volume.
• Sugar: Just a teaspoon can balance out any tartness, especially if your tomatoes are on the acidic side.
• Heavy cream or whole milk: Optional but wonderful, it smooths out the edges and gives the soup a velvety richness.
• Sandwich bread: Any sturdy white or whole wheat works, just avoid anything too airy or it will fall apart in the skillet.
• Sharp cheddar cheese: The sharper the better for these croutons, it holds up to heat and adds a tangy punch.
• Unsalted butter: Softened butter spreads easily and helps the bread crisp up to golden perfection.

Instructions

Preheat and Prep:

Set your oven to 400°F and line a baking sheet with parchment if you want easy cleanup. Halve the tomatoes and arrange them cut side up so they roast evenly and their juices pool instead of running off.

Season and Roast:

Nestle the onion quarters and garlic cloves among the tomatoes, then drizzle everything generously with olive oil and sprinkle with salt, pepper, and your chosen herb. Roast for 25 to 30 minutes until the tomatoes are soft, jammy, and their edges start to char.

Build the Soup Base:

Scrape all the roasted vegetables and any caramelized juices into a large pot. Add the vegetable broth, tomato paste, and sugar if you're using it, then bring everything to a gentle simmer over medium heat for 10 minutes to let the flavors meld.

Blend Until Smooth:

Use an immersion blender right in the pot to puree the soup until it's silky, or work in batches with a countertop blender, being careful with the hot liquid. Stir in the cream or milk if you want extra richness, then taste and adjust the seasoning.

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 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 scatter the grilled cheese croutons on top. They'll stay crispy for a few minutes before softening into cheesy, soupy bites.

Save

There was an evening last fall when I made a double batch of this soup and froze half for later. When I thawed it in January, the smell alone brought me back to that September afternoon when the kitchen windows were still open and the breeze smelled like rain. It's funny how a bowl of soup can hold a season inside it.

Choosing Your Tomatoes

I've made this with everything from heirloom tomatoes to plain grocery store rounds, and while heirlooms add a subtle complexity, any ripe tomato will work as long as it smells sweet when you bring it close to your nose. In winter, I've even used Roma tomatoes and boosted the flavor with an extra tablespoon of tomato paste. The key is roasting them long enough that their natural sugars concentrate and their skins start to wrinkle and char. If your tomatoes are watery, roast them a few minutes longer until they look jammy and collapsed.

Making It Your Own

This soup is endlessly adaptable once you understand the basic method. I've stirred in a handful of fresh basil at the end for a bright, herbal finish, or swirled in a spoonful of pesto right before serving. A pinch of smoked paprika adds a subtle smokiness that makes people ask what your secret is. For the croutons, try Gruyère for a nutty twist or mozzarella if you want extra melt. One time I used sourdough bread and the tangy crust added an unexpected layer that everyone loved.

Storage and Reheating

The soup keeps beautifully in the fridge for up to four days and actually tastes better the next day as the flavors deepen. I store it in a glass jar with a tight lid and reheat it gently on the stovetop, adding a splash of broth or water if it's thickened too much. The grilled cheese croutons, however, don't store well, they turn soggy within an hour. If I'm meal prepping, I make the soup ahead and fry fresh croutons right before serving.

• Freeze the soup in portions for quick weeknight meals, it thaws perfectly and reheats without separating.
• If you're short on time, make the soup in the morning and the croutons right before dinner.
• Leftover roasted tomatoes can be tossed with pasta or spread on toast, they're too good to waste.

Save

This soup has become my answer to gray days and unexpected guests, to using up what's ripe and to feeding people something that feels like care in a bowl. I hope it does the same for you.

Recipe FAQ

→ Can I make this soup ahead of time?

Yes, the soup keeps well for up to 4 days in the refrigerator. Reheat gently on the stovetop and prepare fresh croutons just before serving for best texture and taste.

→ What's the best way to blend the roasted vegetables?

An immersion blender is ideal for creating a smooth texture while keeping everything in the pot. If using a countertop blender, work in batches and let the soup cool slightly to avoid burns.

→ How do I prevent the soup from becoming too acidic?

Adding a teaspoon of sugar helps balance the tomato acidity. You can also use sweeter tomato varieties or roast the tomatoes longer to develop more natural sweetness. Taste as you go and adjust accordingly.

→ Can I substitute the heavy cream?

Absolutely. Whole milk, half-and-half, or plant-based alternatives like oat or cashew cream all work well. You can also omit cream entirely for a lighter version while maintaining rich flavor.

→ What cheese works best for the croutons?

Sharp cheddar provides excellent flavor and melts beautifully, but mozzarella, Gruyère, or fontina are wonderful alternatives. Choose a cheese that melts smoothly for the best texture in the croutons.

→ How do I make this dish vegan?

Use plant-based butter, dairy-free cheese alternatives, and coconut cream or cashew cream instead of heavy cream. The roasting method and flavor profile remain unchanged, creating a satisfying vegan option.