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How to make tomato soup and grilled cheese

Easy Tomato Soup with Pesto Grilled Cheese

  • Author: Geoff
  • Prep Time: 15 minutes
  • Cook Time: 45
  • Total Time: 1 hour
  • Yield: 7-10 servings 1x


this creamy smooth tomato soup with pesto grilled cheese will bring summer into the coldest winter day!



for the soup:

2-each 28-ounce canned of whole peeled tomatoes, run through the course plate in a food mill.

1 medium onion, diced

1 fennel bulb, washed, trimmed of stems and chopped

3 medium carrots, washed, peeled, and chopped

1 tablespoon of coriander seed, toasted and ground with a mortar and pestle

1 teaspoon of fennel seeds, toasted and ground with a mortar and pestle

1 teaspoon of sugar

2 tablespoons of kosher salt

1/2 teaspoon of fresh ground black pepper

1 bunch of basil, tied tightly with kitchen twine (leave a 4-inch string at the top)

for the grilled cheese (per sandwich):

2 slices of your favorite bread, I used Ezekial Sesame. If you slice your own use 1/3 of inch slices.

2 eggs, beaten

1/2 cup cream

1 teaspoon of kosher salt

34 grinds of fresh black pepper

1 large ball (8 ounce) of buffalo mozzarella, cut into 1/4 inch slices

2 tablespoons of basil pesto

1 tablespoon of unsalted butter



1. Tie the basil together with butcher twine leaving a 4-inch piece of string that will be used to tie the basil to the pot handle.

2. Toast the coriander and fennel seed in a dry small saute pan over medium heat until you smell the fragrance of the spices. Grind with a mortar and pestle, then sift the husks, leaving the powder.

3. In a dutch oven over medium heat, add the fennel, carrot, onion, and garlic. Sprinkle with salt and sweat the vegetable for 3-5 minutes until the carrots are tender.

How to make tomato soup and grilled cheese

4. Add the pureed tomatoes, ground spices, and tie the basil to the pot handle and submerge it into the young soup. Bring to a simmer over medium heat and lower to a gentle simmer. Cover, leaving just a small opening to allow steam to escape. Simmer for 45 minutes or until the vegetables are cooked through with no bite. It’s key that you don’t overcook this soup as keeping the flavor of the fennel and carrots will give you a more interesting soup.

How to make tomato soup and grilled cheese

5. When the soup is cooked remove basil (see how easy that is!).

6. Puree the soup in a high-speed blender. (my Vita-Mix is in the shop so I used my Nutri-Bullet!). If you did not run the whole peeled tomatoes through a food mill to remove the seeds and unwanted fibers, you can do so now by straining the soup through a china-cap or large mesh strainer. This will ensure that the soup will be silky and smooth. 

How to make tomato soup and grilled cheese

7. Heat a cast iron or carbon steel pan on medium heat. Shingle the cheese on one side of the bread. Spread a generous portion of pesto on the other side. Press the sandwich rather firmly together. Quickly dip into the egg/milk mixture. Flip and repeat. You don’t want to soak the bread, just coat it. 

8. Add the butter to the pan. Keep the medium heat. When the butter dissolves and begins to brown, add the sandwich. Cook for 2 minutes and check to see if the sandwich is browned. If so, flip and cook for 2-3 more minutes. If the cheese is not fully melted lower the heat and cook longer swirling the sandwich so it doesn’t burn. The cheese should be fully melted. Remove, cut off the crusts (or not), and enjoy with your soup!

How to make tomato soup and grilled cheese





  • If you can’t find Buffalo Mozzarella, shredded whole milk mozzarella will work just fine.
  • If you’re not into fennel, substitute celery and omit the fennel seed.
  • Category: Soup
  • Method: Stovetop
  • Cuisine: Mediterranean

Keywords: Tomato and Grilled Cheese, Buffalo Mozzarella, Buffala, Winter soup