Tomato Basil Soup and Grilled Cheese Croutons

This is cozy, cheesy, comforting goodness. The half & half in the soup is optional, you can omit if you’re dairy-free or trying to cut back on calories. I’d recommend adding it because it’s a small amount relative to the quantity of the soup (and half & half is a lot lighter than most recipes using heavy cream), and it adds that extra bit of creamy, velvety goodness.

This makes a big ol’ batch of soup because I love leftovers and it freezes extremely well. The soup makes enough for approximately 6-8 servings, but you could easily cut the recipe in half. The grilled cheese croutons serve somewhere between 2-4 depending on how many croutons you want (and I want a whole sandwich worth of croutons).


For the tomato basil soup:

  • 4 28-oz cans peeled San Marzano tomatoes
  • 1 large white or yellow onion, quartered
  • 3 tbsp salted butter
  • 1 tbsp dried oregano
  • 5 cloves garlic, smashed
  • Handful of fresh basil leaves
  • 1 tsp red pepper flakes (or more, depending on spice preference)
  • 1 cup half & half (optional)
  • Fine sea salt
  • 1 tbsp chives, finely chopped, for garnish

For the grilled cheese croutons:

  • 2 tbsp butter, softened
  • 4 slices white bread
  • 2 slices american cheese
  • 2 oz shredded cheddar cheese


  1. In a large dutch oven or stockpot, add the tomatoes, onion, butter, oregano, garlic, basil, and red pepper flakes. Bring to a boil while stirring occasionally, and using a wooden spoon to break up the tomatoes into smaller pieces. Reduce the heat to low, cover the pot with a lid, and simmer for 45-60 minutes.
  2. Puree with an immersion blender (alternatively, you can use a blender, working in batches). Stir in the half & half (if using). Season to taste with salt (I typically start with 1 tsp and go from there). Cover the soup with the lid and keep warm while you make the grilled cheese croutons.
  3. Heat a grill pan or a nonstick skillet over medium heat. Spread the butter over one side of each bread slice (approx 1/2 tbsp per slice of bread). Turn the slices over and top each of two of the slices with a slice of american cheese and half of the shredded cheddar. Place the remaining two slices of bread on top, buttered side up. Transfer the sandwich to the pan and grill until the bread is toasted and golden and the cheese is melted. Let cool for a few minutes and cut into cubes.
  4. Ladle the soup into the bowls, top with the grilled cheese croutons and a sprinkle of chives, and enjoy immediately.