Healthy Tomato Basil Soup with Pesto Grilled Cheese

The ultimate fancy, grown-up grilled cheese made with pesto, basil, havarti and mozzarella melted between perfectly toasted whole wheat bread to eat with/dunk in a bowl of flavorful, rich tomato basil soup. A match made in food heaven.

I can’t believe how cold it is in Chicago already! Only 14 degrees today. Yesterday, it was only 1 degree. WHAT?!? It’s literally bone chilling, can’t feel your face COLD. It’s time to officially get out the snow boots, heavy duty winter coats, fleece-lined gloves, wool scarves, and ski hats. This is my least favorite part about winter – the amount of time needed to bundle up just to go outside and face the day. Then having to undo it all when you get to your destination. It prevents me from wanting to go outside at all. Commence winter hibernation mode.

One advantage to this cold season – it’s time to make delicious, soul-warming foods, like soups, stews, and chili. My favorite winter treat is tomato soup and grilled cheese. There is something so nostalgic and comforting about this classic pairing. When I was younger, we would make the traditional grilled cheese with the slices of American Kraft singles between 2 pieces of Wonder white bread to eat with Campbell’s tomato soup. Simple and delicious.

As an adult, I crave a slightly more sophisticated version of this combo. That’s why I decided to elevate this childhood favorite. Enter the pesto Havarti mozzarella grilled cheese with tomato basil soup. This is a much more flavorful and healthier version, since it is made from scratch with fresh, wholesome ingredients.

Let’s get to cooking.

This is a multi-step process as there are three components to this dish: the soup, the pesto, and the grilled cheese.

We will start with the soup. The soup comes together in under an hour. In a large soup pot, heat olive oil and add onions, garlic, a touch of salt and pepper, and red pepper flakes. The onions, garlic, and red pepper flakes help to make the soup flavorful. Even if you are not an onion fan, I highly recommend using them in this soup – it is all pureed in the end so you won’t even know they are there, but your soup will be vibrant and delicious.

Once the onions are translucent and the garlic fragrant, about 2-3 minutes, add the balsamic, Worcestershire, and tomato paste. My secret ingredients in this recipe are the balsamic and Worcestershire  – they add another depth of flavor to the dish – umami and a touch of sweetness. Let these ingredients cook slightly to bring out their flavors, about 2 minutes.

The intensive part of cooking the soup is already done. You just need to add the remaining ingredients (except brown sugar) and let the soup simmer for 30 minutes on the stove so all the flavors meld together and the tomatoes break down and release their juices. Another secret ingredient is the parmesan rind. It adds a slightly nutty flavor that goes well with the walnut pesto. Any time you buy fresh parmesan, save the rind for soups like this. But if you do not have a parmesan rind, you can skip this step and your soup will still be yummy.

Once the soup is done simmering, remove the bay leaf. Finally, use an immersion blender to puree the soup until it is smooth. At this point, I tasted the soup so I could adjust seasonings. I added a 1/2 tablespoon of brown sugar (or any sweetner of choice) to round out the acidic flavor from the tomatoes. This is completely optional – you can decide once you taste the soup if you think it needs a touch of sweetness. I also added a little more salt and pepper to get it just right.

While the soup is simmering, you should make the pesto and grilled cheese. To make the pesto, you just need to add all the ingredients to a food processor and pulse into well-combined and only slightly chunky. As you blend the pesto, you can add a little more olive oil and lemon juice if it is too thick. This is a small batch of pesto, so it will be enough for about 6 sandwiches.

Time to assemble the grilled cheese. I used Angelic Bakehouse whole wheat bread as my base. This is my favorite sandwich bread because it is low in calories and made with real, natural ingredients but still tastes great.

Add a little bit of butter or olive oil to the outside of the slices of bread. On the inside of one slice of bread, add about a tablespoon of the pesto and then pile on the two cheeses and fresh basil, and top it with the other slice of bread, butter side up. Heat a skillet with olive oil and add the sandwich, butter face down. Cook the sandwich for 2-3 minutes on each buttered side until golden brown. I finished my grilled cheese in a 400-degree oven so the cheese was fully melted and amazingly gooey.

I will admit this is more work than the traditional grilled cheese I ate as a child, but well worth it. Both the grilled cheese and tomato soup are flavor bombs. The grilled cheese is gooey, salty, and creamy with a great crunch from the toasted whole wheat bread. The soup is well-balanced, bold, savory, with a touch of sweetness, and extra herbaceous flavor from the basil. For pure magic, I highly recommend dumping the grilled cheese into the warm soup so you can enjoy both together. Prepared to break into a happy dance. It’s that good.

I can certainly deal with the winter months if I get to enjoy delicious comfort food like grilled cheese and tomato soup. I would even get completely bundled up to travel for a bite of this goodness. I hope you love it too!

Healthy Tomato Basil Soup with Pesto Havarti Mozzarella Grilled Cheese

A creamy, rich healthy tomato soup paired with the ultimate grilled cheese. A match made in food heaven. 

Course Main Course
Cuisine American
Prep Time 20 minutes
Cook Time 30 minutes
Total Time 50 minutes
Servings 6 servings
Author Dani


Tomato Soup

  • 1 medium sweet onion
  • 1 tablespoon olive oil
  • 3 gloves garlic
  • 2 tablespoons balsamic vinegar
  • 1 tablespoon Worcestershire optional
  • pinch red pepper flakes to taste
  • 2 tablespoons tomato paste
  • 28 ounce can of whole marzano tomatoes
  • 1 1/2 cups chicken broth low sodium, use vegetable broth if vegan or vegetarian
  • 1/2 tablespoon brown sugar
  • 1 parmesan rhine optional
  • 2 bay leaves
  • 5-6 basil leaves julienned
  • 1 tablespoon greek yogurt topping, optional

Walnut Pesto

  • 1/4 cup toasted walnuts
  • 1 ounce container basil
  • juice of half of a lemon
  • 1/4 cup parmesan
  • 1 teaspoon garlic
  • 1/4 cup olive oil

Pesto Grilled Cheese

  • 1 tablespoon walnut pesto
  • 2 slices havarti
  • 2 slices fresh mozzarella
  • 2 basil leaves
  • 1 tablespoon butter
  • 1 tablespoon olive oil
  • 2 slices whole wheat bread


Tomato Soup

  1. In a large soup pot, heat the olive oil. Add the onions , red pepper flakes and garlic and cook until fragrant and the onions are translucent. About 2-3 minutes. 

  2. Next, add the balsamic, Worcestershire, and tomato paste and cook for 2 minutes. 

  3. Finally, add the whole tomatoes, broth, basil, and bay leaves and mix until well incorporated. 

  4. Simmer for 30 minutes so the flavors develop and the tomatoes break down.

  5. Remove basil leaf. Add 1/2 tablespoon brown sugar. Taste and adjust seasonings as needed (more salt, pepper, and red pepper flakes if desired).

  6. Use an immersion blender to puree the soup until smooth. If you do not have an immersion blender, you can also transfer the soup in batches into a blender and blend until smooth.

  7. Top with greek yogurt, extra basil, and toasted walnuts. 

  8. Serve and enjoy! 

Walnut Pesto

  1. Add all of the ingredients into a food processor and blend until well-incorporated. You can add extra olive oil or lemon juice if pesto is too thick. 

  2. Transfer to an airtight container.

  3. You can store the pesto in your fridge up to a week. 

Pesto Grilled Cheese

  1. Butter the outside portion of the bread slices.

  2. Slather on the pesto to one slice of the bread (the side not already buttered).

  3. Top the pesto with basil leaves and cheeses. Finally, add on the other slice of bread, the non buttered side touching the cheese.

  4. Heat olive oil in a nonstick pan. Place one of the buttered sides of the bread down on the hot olive oil. Let cook for 2 minutes or until golden brown. Flip and cook on other side.

  5. May need to finish in a 400 degree oven for 3-5 minutes so the cheese fully melts.

  6. Serve and enjoy! 

Recipe Notes

Dunking you grilled cheese into the soup is highly recommended.