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Cozy Slow-Roasted Tomato Soup with Grilled Cheese Croutons

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A deeply flavorful tomato soup made by slow-roasting Roma tomatoes with garlic and onion, then blended with cream and balsamic vinegar. Topped with crispy, buttery grilled cheese croutons for the ultimate comfort meal.

Ingredients

Scale
  • 3 pounds Roma or plum tomatoes, halved lengthwise
  • 6 cloves garlic, peeled
  • 1 medium yellow onion, quartered
  • 3 tablespoons olive oil
  • 1 teaspoon kosher salt
  • 1/2 teaspoon black pepper, freshly ground
  • 1/2 teaspoon dried oregano
  • 1/4 teaspoon red pepper flakes (optional)
  • 2 cups low-sodium vegetable broth
  • 1/2 cup heavy cream
  • 1 tablespoon balsamic vinegar
  • 2 tablespoons unsalted butter
  • 8 slices sourdough bread, cut into 1-inch cubes
  • 4 tablespoons unsalted butter, softened
  • 2 cups sharp cheddar cheese, shredded
  • 1/4 teaspoon garlic powder (optional)
  • Fresh basil leaves, chiffonaded (for garnish)
  • Extra drizzle of olive oil or heavy cream (for garnish)
  • Flaky sea salt like Maldon (for garnish)

Instructions

  1. Preheat your oven to 400°F (200°C). Position a rack in the middle of the oven. Line a large rimmed baking sheet with parchment paper.
  2. Prepare the tomatoes and aromatics. Halve all the Roma tomatoes lengthwise. Place them cut-side up on the prepared baking sheet. Tuck the garlic cloves and onion quarters in between the tomatoes. Drizzle everything with olive oil, then sprinkle with salt, pepper, oregano, and red pepper flakes if using. Use your hands to gently toss everything so it’s coated. Arrange the tomatoes cut-side up again.
  3. Roast for 45-55 minutes. The tomatoes should be deeply wrinkled and starting to brown at the edges. The garlic should be soft and golden. The onions should look translucent and slightly charred. Halfway through, rotate the pan for even roasting.
  4. While the tomatoes roast, make the grilled cheese croutons. Spread the softened butter on all sides of the bread cubes. In a large skillet over medium heat, work in batches to toast the bread cubes until golden on all sides, about 2-3 minutes per batch. Transfer to a plate. Once all cubes are toasted, return them to the skillet, reduce heat to low, and sprinkle the shredded cheddar over the top. Toss gently until the cheese melts and clings to the bread. Spread them back out on the plate to cool…
  5. Transfer the roasted tomatoes to a Dutch oven. Scrape everything from the baking sheet into the pot—including all the caramelized bits and juices. Add the vegetable broth and bring to a simmer over medium heat. Let it bubble gently for 5 minutes to meld the flavors.
  6. Blend the soup until smooth. Use an immersion blender directly in the pot. Blend until completely smooth, about 1-2 minutes. If using a regular blender, work in batches and fill it no more than halfway. Hold the lid down with a folded kitchen towel and blend on low, then increase speed. Return the blended soup to the pot.
  7. Finish the soup. Stir in the heavy cream, balsamic vinegar, and butter. Keep stirring until the butter melts completely. Taste and adjust seasoning. Simmer on low for another 5 minutes, stirring occasionally.
  8. Serve immediately. Ladle the soup into bowls. Top with a generous handful of grilled cheese croutons. Garnish with fresh basil, a drizzle of olive oil, and a pinch of flaky sea salt.

Notes

For an ultra-smooth soup, strain through a fine-mesh sieve after blending. The soup tastes even better the next day. Store croutons separately to maintain crispness.

Nutrition

Keywords: tomato soup, grilled cheese croutons, slow-roasted, comfort food, vegetarian, fall recipe, winter recipe

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