Roasted Tomato Soup with Grilled Cheese Croutons

My neighbor brought over a pot of this soup one November afternoon when I had a cold, and I still think about how the roasted tomatoes smelled sweeter than any canned version I'd tried. The grilled cheese cubes floating on top weren't soggy—they stayed crisp enough to scoop up with my spoon. I asked for the recipe immediately. She laughed and said it was just tomatoes and patience. That week, I made it twice.

I served this to my kids on a rainy Saturday, and they fought over the croutons before the soup even cooled down. My daughter dipped hers like tortilla chips, my son stacked three on his spoon at once. I realized then that this wasn't just soup—it was the kind of meal that made them sit at the table longer, asking questions about how the tomatoes got so red in the oven. We ended up making grilled cheese croutons for salads the next week.

Ingredients

• Ripe tomatoes: Choose tomatoes that feel heavy and smell faintly sweet at the stem, roasting concentrates their flavor so quality matters here.
• Onion and garlic: Roasting them whole mellows the sharpness and adds a caramelized sweetness that balances the acidity of the tomatoes.
• Olive oil: Use enough to coat everything lightly, it helps the vegetables brown and keeps them from drying out in the oven.
• Vegetable broth: Low sodium is best so you can control the saltiness, chicken broth works too if that's what you have.
• Heavy cream or milk: This is optional but it turns the soup silky and rounds out the roasted flavors, you can skip it for a lighter version.
• Sharp cheddar cheese: The sharper the better for the croutons, it stands up to the tomato and doesn't get lost in the soup.
• Sandwich bread: Soft white or whole wheat both work, just make sure it's sturdy enough to hold the cheese without falling apart.
• Butter: Softened butter spreads more evenly and gives the croutons that golden, crispy edge.

Instructions

Roast the vegetables:

Arrange the tomatoes cut side up so they hold their juices while roasting, and nestle the onion and garlic around them. Drizzle everything with olive oil and season generously, the oven will do the rest.

Simmer the soup base:

Scrape every bit of caramelized tomato and onion into the pot, those browned edges are where the flavor lives. Let it simmer gently so the broth absorbs all the roasted sweetness.

Blend until smooth:

If using a countertop blender, fill it only halfway and hold the lid down with a towel to avoid hot splashes. An immersion blender is easier and lets you control the texture right in the pot.

Stir in cream:

Add it off the heat and stir slowly so it doesn't curdle. Taste and adjust the salt, sometimes a pinch of sugar helps if your tomatoes were very tart.

Make the grilled cheese croutons:

Butter the outsides well and press the sandwich gently in the pan so the cheese melts evenly. Let them cool for a minute before cutting or the cheese will ooze out everywhere.

Serve hot:

Ladle the soup into bowls and scatter the croutons on top just before serving. They'll soften slightly but still keep enough crunch to contrast with the soup.

Save

The first time I brought this to a potluck, someone asked if I'd used heirloom tomatoes or added balsamic vinegar. I hadn't done either, just roasted regular grocery store tomatoes long enough for them to collapse into themselves. That's when I understood that time in the oven can make ordinary ingredients taste special. The grilled cheese croutons sealed the deal, people went back for seconds just to get more of them.

How to Store and Reheat

The soup keeps in the fridge for up to four days in an airtight container, and it actually tastes better the next day once the flavors settle. Reheat it gently on the stove over low heat, stirring occasionally so the cream doesn't separate. I don't recommend freezing it if you've added cream, but the base without dairy freezes beautifully for up to three months. Make the grilled cheese croutons fresh each time, they lose their crispness if stored and reheated.

Variations to Try

I've added roasted red bell peppers to the tomatoes for a slightly sweeter, smokier soup that my husband loves. A handful of fresh basil stirred in at the end brightens everything up, especially in summer when basil is everywhere. For the croutons, I've used Gruyère and sourdough bread, which made them taste fancier without any extra work. Once I ran out of bread and used thick crackers with cheese melted on top, it wasn't the same but it worked in a pinch.

Serving Suggestions

This soup is perfect with a simple green salad dressed in lemon and olive oil, the brightness cuts through the richness. I've also served it alongside roasted vegetables or a slice of crusty bread if I'm feeding a crowd. For kids, I put the croutons on the side so they can dunk them like fries, which makes them more likely to finish their bowls.

• Top with a drizzle of good olive oil and a few fresh thyme leaves for a restaurant style presentation.
• Pair it with a crisp white wine or sparkling water with lemon if you want something light.
• Double the crouton recipe, they disappear fast and everyone will ask for more.

Save

This soup has become my answer to cold nights and last minute dinner guests, it feels generous without being complicated. I hope it finds a spot in your regular rotation the way it has in mine.

Recipe FAQs

→ Can I make this soup ahead of time?

Yes, the soup base stores well in the refrigerator for up to 4 days or freezes for up to 3 months. Prepare the grilled cheese croutons fresh before serving for optimal crispness, or store them in an airtight container for 2 days and reheat in a 350°F oven for 5 minutes.

→ What type of tomatoes work best?

Use ripe, in-season tomatoes like Roma, Beefsteak, or heirloom varieties for the richest flavor. If fresh tomatoes aren't available, high-quality canned whole tomatoes (about 28 oz) can substitute effectively.

→ How do I achieve a perfectly creamy texture?

An immersion blender creates the smoothest consistency by breaking down all tomato solids evenly. For extra creaminess, add heavy cream or whole milk in the final step. Ensure you blend thoroughly for a velvety result.

→ Can I customize the cheese for the croutons?

Absolutely. Sharp cheddar provides a classic bite, but Gruyère offers nutty depth, mozzarella brings mild creaminess, or even aged Gouda works beautifully. Experiment with your favorite melting cheeses.

→ How do I make this dairy-free?

Substitute plant-based butter and vegan cheese alternatives for the croutons, and use coconut cream or cashew cream instead of heavy cream in the soup. Quality dairy-free cheeses that melt well are essential for successful croutons.

→ What additions enhance the flavor?

Smoked paprika adds depth, fresh basil provides herbal brightness, a touch of balsamic vinegar introduces complexity, or a pinch of red pepper flakes brings subtle heat. Taste and adjust seasonings throughout cooking.