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Roasted Tomato Basil Soup with Grilled Cheese

This Roasted Tomato Basil Soup with Grilled Cheese is the ultimate comfort food. Fresh cherry tomatoes, Roma tomatoes, sweet onion, and garlic are roasted until tender, then blended with fresh basil, chicken broth, and cream for a rich, silky soup. Served with a golden sourdough grilled cheese filled with aged cheddar and Gruyère, it's a nostalgic childhood favorite with a little something extra.
Prep Time15 minutes
Cook Time1 hour 30 minutes
Total Time1 hour 45 minutes
Servings: 4 Servings

Ingredients

For the Roasted Tomato Soup

  • 24 oz Fresh Cherry Tomatoes
  • 2 15oz cans Baby Roma (I like to use Mutti)
  • 1 sweet onions quartered
  • 1 head of garlic
  • 2 cups chicken broth divided
  • 1/2 cup heavy cream
  • 1 large handful fresh basil plus more as needed
  • Red Pepper Flakes to taste
  • Salt & Pepper to taste
  • EVOO as needed
  • Parmigiano Reggiano freshly grated, to taste

For the Grilled Cheese

  • Sourdough Bread 2 slices per sandwich
  • Aged Cheddar cheese 2 slices per sandwich
  • Gruyère cheese freshly grated, a generous handful per sandwich
  • Unsalted butter as needed
  • EVOO a small drizzle in the skillet