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Creamy Roasted Tomato Basil Soup with Easy Grilled Cheese Croutons

roasted tomato basil soup - featured image

This creamy roasted tomato basil soup is silky, velvety, and packed with deep, sweet richness from caramelized tomatoes. Topped with buttery, crispy grilled cheese croutons, it’s the ultimate comfort food for chilly evenings.

Ingredients

Scale
  • 2 pounds Roma tomatoes, halved lengthwise
  • 1 head of garlic, top sliced off to expose the cloves
  • 2 tablespoons olive oil, plus more for drizzling
  • 1 medium yellow onion, diced (about 1 cup)
  • 2 cups vegetable broth (or chicken broth for richer flavor)
  • 1 cup fresh basil leaves, loosely packed (plus more for garnish)
  • 1/2 cup heavy cream (or full-fat coconut milk for dairy-free)
  • 1 teaspoon salt, plus more to taste
  • 1/2 teaspoon black pepper
  • 1/4 teaspoon red pepper flakes (optional)
  • 1 tablespoon balsamic vinegar
  • 4 slices sourdough bread (or any sturdy bread)
  • 2 tablespoons butter, softened (salted butter works best)
  • 4 ounces sharp cheddar cheese, thinly sliced or shredded
  • 2 ounces provolone or mozzarella, for extra meltiness

Instructions

  1. Preheat oven to 400°F (200°C). Line a baking sheet with parchment paper. Arrange halved Roma tomatoes cut-side up on the sheet. Place the halved head of garlic on a small piece of foil, drizzle with 1 teaspoon olive oil, and wrap tightly. Nestle the foil packet on the baking sheet with the tomatoes. Drizzle tomatoes with 1 tablespoon olive oil and sprinkle with a pinch of salt and pepper. Roast for 35-40 minutes until tomatoes are wrinkled, soft, and caramelized.
  2. While tomatoes roast, heat remaining 1 tablespoon olive oil in a large soup pot over medium heat. Add diced onion and cook for 5-6 minutes, stirring occasionally, until translucent and starting to brown at the edges.
  3. Once tomatoes are done, carefully unwrap the garlic and squeeze the soft, caramelized cloves into the pot with the onions. Add roasted tomatoes along with any juices from the baking sheet. Pour in vegetable broth and add fresh basil leaves. Use an immersion blender to blend until completely smooth. (If using a regular blender, work in batches and hold the lid firmly.)
  4. Return the pot to low heat. Stir in heavy cream, salt, pepper, and red pepper flakes if using. Let simmer gently for 5 minutes to meld flavors. Taste and adjust seasoning. Stir in balsamic vinegar right before serving.
  5. While soup simmers, heat a large skillet over medium heat. Butter one side of each sourdough slice. Place two slices butter-side down on a plate. Layer cheddar and provolone on top, then top with remaining bread slices, butter-side up. Cook sandwiches in the hot skillet for 3-4 minutes per side until golden brown and cheese is fully melted. Let rest for a minute, then cut into 1-inch cubes.
  6. Ladle hot soup into bowls. Pile a generous handful of grilled cheese croutons in the center. Garnish with fresh basil leaves and a drizzle of olive oil if desired. Serve immediately.

Notes

For the creamiest soup, let the immersion blender run for a full 60 seconds. Don’t crowd the tomatoes on the baking sheet to ensure proper caramelization. Add basil right before blending to keep it bright green. Don’t skip the balsamic vinegar—it brightens the soup. For croutons, use day-old bread if available. The soup can be stored in the refrigerator for up to 5 days or frozen for up to 3 months (freeze without cream for best texture).

Nutrition

Keywords: tomato soup, roasted tomato soup, basil soup, grilled cheese croutons, comfort food, creamy soup, fall recipe, winter soup