Roasted Tomato Soup with Grilled Cheese

Featured in: Weeknight Dinners

Transform fresh tomatoes into silky soup by roasting them with onions and garlic until caramelized, then simmering with vegetable broth and tomato paste for deep, rich flavor. Create bite-sized grilled cheese croutons by sandwiching sharp cheddar between buttered bread and toasting until golden. The combination of warm, creamy soup with crispy, cheese-filled croutons delivers ultimate comfort in every spoonful—ready in just one hour.

Updated on Sun, 18 Jan 2026 12:21:00 GMT
Creamy roasted tomato soup with grilled cheese croutons, garnished with fresh basil, served in a rustic white bowl. Save
Creamy roasted tomato soup with grilled cheese croutons, garnished with fresh basil, served in a rustic white bowl. | milestonepan.com

My daughter came home from school one rainy Thursday asking if we could have "the kind of soup that tastes like a hug." I had a bag of tomatoes softening on the counter and a loaf of bread that needed using. What started as a quick fix turned into one of those meals where everyone went quiet at the table, just eating. The roasted tomatoes made all the difference, turning simple ingredients into something that felt like I'd been simmering it all day.

I made this for my sister when she visited last winter, and she kept dipping the croutons until her bowl was empty, then asked if there was more. We sat by the window watching the snow fall, bowls in our laps, talking about nothing important. It was one of those meals that became a memory without trying. Now every time she calls, she asks if I've made "that tomato thing" again.

Ingredients

  • Ripe tomatoes: Use the ripest ones you can find, even if they're a little soft, because roasting concentrates their flavor and sweetness beautifully.
  • Onion and garlic: Roasting them alongside the tomatoes mellows their sharpness and adds a deep, caramelized backbone to the soup.
  • Olive oil: A good drizzle helps everything roast evenly and adds a subtle richness that carries through the finished soup.
  • Vegetable broth: This thins the soup to the perfect consistency, and using a quality broth makes a noticeable difference in the final taste.
  • 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 rounds out any acidity from the tomatoes.
  • Sharp cheddar cheese: The sharpness stands up to the richness of the butter and adds a bold flavor to the croutons.
  • Sandwich bread: Any sturdy white or whole wheat works, just avoid anything too soft or it will fall apart in the pan.
  • Unsalted butter: Softened butter spreads easily and creates that golden, crispy crust on the grilled cheese.

Instructions

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Roast the vegetables:
Arrange the halved tomatoes cut side up on a baking sheet with the onion and garlic, 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, slightly charred at the edges, and their juices have pooled on the pan.
Simmer the soup base:
Transfer all the roasted vegetables and their juices into a large pot, add the vegetable broth, tomato paste, and a teaspoon of sugar if your tomatoes are tart. Let it simmer gently over medium heat for about 10 minutes, stirring now and then so nothing sticks.
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 and velvety. Stir in the cream or milk if you want it richer, then taste and adjust the salt and pepper.
Make the grilled cheese croutons:
Butter one side of each bread slice, sandwich the cheese between two slices with the buttered sides facing out, and cook in a skillet over medium heat until golden and crispy, about 2 to 3 minutes per side. Let them cool just enough to handle, then cut into bite sized cubes.
Serve:
Ladle the hot soup into bowls and top each one with a handful of grilled cheese croutons. Serve immediately while the croutons are still warm and crispy.
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Roasted tomato soup with grilled cheese croutons beside grilled cheese sandwich halves and ripe tomatoes on a wooden table. Save
Roasted tomato soup with grilled cheese croutons beside grilled cheese sandwich halves and ripe tomatoes on a wooden table. | milestonepan.com

One night I served this to friends who claimed they didn't like tomato soup, and they finished two bowls each without saying a word. When I brought out seconds, one of them finally looked up and said, "Okay, this is different." It was the roasting, the cream, and those little grilled cheese bites that won them over. Sometimes the best compliment is just an empty bowl.

Making It Your Own

A pinch of smoked paprika stirred into the soup just before blending adds a gentle smokiness that makes it taste like it came from a wood fired oven. You can also swap the cheddar in the croutons for mozzarella if you want them milder and stretchier, or try Gruyère for something a little more grown up. If you want to make this vegan, use plant based butter, cheese, and a cashew cream or coconut milk in place of the dairy, and it still turns out wonderfully rich.

Storing and Reheating

The soup keeps in the fridge for up to four days in an airtight container, and it actually tastes even better the next day after the flavors have had time to settle. Reheat it gently on the stove over low heat, adding a splash of broth or water if it has thickened. Make the grilled cheese croutons fresh each time you serve it, because they lose their crispness once they sit, and half the magic is in that crunch.

Serving Suggestions

This soup is perfect on its own for a light dinner, but I like to serve it with a simple green salad dressed in lemon and olive oil to balance the richness. If you're feeding kids, let them dip the croutons themselves, it turns the meal into something interactive and fun. On colder nights, I sometimes add a drizzle of good olive oil and a few fresh basil leaves on top, and it feels almost fancy.

  • Serve with a crisp arugula salad tossed in balsamic vinaigrette.
  • Pair it with a crusty baguette for dipping if you want even more bread.
  • Top with extra croutons and a sprinkle of fresh thyme for a restaurant style presentation.
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Velvety roasted tomato soup topped with crispy grilled cheese croutons, ready to serve on a cozy kitchen counter. Save
Velvety roasted tomato soup topped with crispy grilled cheese croutons, ready to serve on a cozy kitchen counter. | milestonepan.com

This soup has become my answer to grey days, surprise guests, and that feeling when you just want something warm and uncomplicated. I hope it becomes that for you too.

Recipe FAQs

Can I make this soup ahead of time?

Yes, the soup keeps well for up to 4 days when refrigerated in an airtight container. Reheat gently on the stovetop or microwave before serving. Prepare croutons fresh on serving day for maximum crispiness.

What type of tomatoes work best?

Roma or plum tomatoes are ideal due to their meaty texture and lower water content. Vine-ripened tomatoes also work wonderfully. Avoid using hothouse tomatoes as they can be watery and lack flavor intensity.

How do I prevent the soup from being too acidic?

Roasting tomatoes naturally caramelizes their sugars and mellows acidity. The optional teaspoon of sugar further balances tartness. If needed, add a pinch more sugar or stir in a splash of heavy cream to neutralize sharp notes.

Can I freeze the croutons?

Grilled cheese croutons are best served fresh for optimal texture. However, you can freeze the grilled cheese sandwiches before cutting into cubes, then briefly toast them in a 350°F oven until heated through and crispy.

What cheese alternatives work well?

Gruyère adds nutty depth, while mozzarella creates a creamier crouton. For a sharper flavor, try aged cheddar or a blend. Vegan alternatives like cashew cheese or commercial dairy-free brands also melt effectively.

Is the heavy cream necessary?

No, it's optional. The roasted tomatoes create natural creaminess when blended. Add cream or whole milk only if you prefer extra richness and silkiness, or use plant-based alternatives for a dairy-free version.

Roasted Tomato Soup with Grilled Cheese

Velvety roasted tomato soup paired with crispy grilled cheese croutons. Comfort food at its finest.

Prep Time
20 min
Time to Cook
40 min
Time Needed
60 min
Created by Caleb Barnes


Skill Level Easy

Cuisine American

Servings Yielded 4 Number of Servings

Special Diets Meatless

What You'll Need

Roasted Tomato Soup

01 1.5 lbs ripe tomatoes, halved
02 1 medium onion, quartered
03 4 garlic cloves, peeled
04 2 tablespoons olive oil
05 1 teaspoon salt
06 0.5 teaspoon black pepper
07 1 teaspoon dried thyme or basil
08 2 cups vegetable broth
09 1 tablespoon tomato paste
10 1 teaspoon sugar
11 0.5 cup heavy cream or whole milk

Grilled Cheese Croutons

01 4 slices sandwich bread
02 4 ounces sharp cheddar cheese, sliced or shredded
03 2 tablespoons unsalted butter, softened

How To Make

Step 01

Preheat oven: Preheat oven to 400°F.

Step 02

Arrange vegetables: Arrange tomatoes cut side up, onion, and garlic on a baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and thyme or basil.

Step 03

Roast vegetables: Roast for 25 to 30 minutes, until tomatoes are soft and caramelized.

Step 04

Prepare soup base: Transfer roasted vegetables including any juices to a large pot. Add vegetable broth, tomato paste, and sugar. Bring to a simmer over medium heat for 10 minutes, stirring occasionally.

Step 05

Blend soup: Using an immersion blender or carefully in batches with a countertop blender, blend soup until smooth. Stir in cream or milk if desired. Adjust seasoning as needed. Keep warm over low heat.

Step 06

Prepare grilled cheese croutons: Butter one side of each bread slice. Place cheese between two slices, buttered sides out. Heat a skillet over medium heat and cook sandwiches until golden brown and cheese is melted, about 2 to 3 minutes per side. Let cool slightly, then cut into 1-inch cubes.

Step 07

Serve: Serve soup hot, topped with grilled cheese croutons.

Tools Needed

  • Baking sheet
  • Large pot
  • Immersion blender or countertop blender
  • Skillet
  • Knife and cutting board

Allergen Details

Review each ingredient for allergens and speak with your healthcare provider if you have questions.
  • Contains wheat from bread
  • Contains milk from cheese, butter, and cream
  • Use gluten-free bread and dairy-free cheese and butter as needed for allergies

Nutrition (per serving)

For informational use only. Always consult with a health professional if needed.
  • Calorie Count: 410
  • Fats: 22 g
  • Carbohydrates: 38 g
  • Proteins: 13 g