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Comfort food: Homemade tomato soup with grilled cheese croutons
Some Kinda Good
tomato soup

On a cold day, there’s nothing quite as comforting as a bowl of homemade soup or hearty chowder. With every spoonful, it’s like a big hug in a bowl. The warmth and flavors simply soothe the soul. 

In a time crunch, there are some delicious canned soups, but nothing quite takes the place of homemade soup. As it simmers on the stovetop, it perfumes the whole house and gets everyone hungry for dinner.  A classic combination is tomato soup with a grilled cheese sandwich, and inevitably, I always dunk my sandwich in my soup. 

To that end, I make a homemade roasted tomato soup with grilled cheese croutons. It’s buttery and creamy, with only one rule: Never use processed American cheese. Only sharp cheddar will do. For the grilled cheese croutons, simply make a grilled cheese sandwich by buttering both sides of bread, layer with sharp cheddar and sauté in a pan until the cheese is hot and bubbly. Slice the sandwich into cubes. To achieve great grill marks, use a grill pan or Panini press.

In the soup, the tomatoes caramelize while roasting and get a rich depth of flavor, and the onion and garlic compliment the tomatoes in a marriage meant to be. I finish the soup with a dollop of sour cream, a splash of heavy cream and some chopped green onions. It really is Some Kinda Good.

Be sure to visit for more cold weather recipes and delicious tips on achieving great depth of flavor. Let’s enjoy the cooler temperatures while they last!

Homemade Tomato Soup for Two


• 1 pound of fresh tomatoes, cut into 

quarters (About 4 medium size)

• 1 medium onion, sliced

• 3 cloves of fresh garlic, smashed

• Handful of heirloom cherry tomatoes

• 3 tablespoons extra virgin olive oil

• Salt and pepper

• Herbes de Provence (You can also use 

any combination of dried Italian herbs)

• 2 ½ to 3 cups of chicken broth

• Splash of heavy cream for finishing

• Sour cream, optional

• Green onion, for garnish


Preheat the oven to 450 degrees. Slice medium tomatoes into quarters and heirloom tomatoes in half. Spread onto a large baking sheet, along with smashed garlic cloves and onion. Drizzle with olive oil and season well with salt and pepper. Toss everything together using clean hands. Roast for 30 minutes. Once vegetables have roasted, if using an immersion blender, transfer vegetables to a large stockpot set over medium heat. Add chicken broth and season with salt and pepper. Blend vegetables to desired consistency. Turn heat to high, cover with a lid and bring to a boil. Reduce liquid until thickened,  about 2-3 minutes. Turn heat to low and simmer for 15-20 minutes. Add a splash of heavy cream and stir. Serve soup in a bowl, with a dollop of sour cream and grilled cheese croutons. Garnish with fresh basil.