Creamy Tomato Basil Soup and The Greatest Grilled Cheese You’ll Ever Eat

Prep Time
15 mins
Cook Time
30 mins


  • For the Creamy Tomato Soup;
  • 1 Medium Yellow Onion diced
  • 1 Large Sweet Onion diced
  • 4 Large cloves of garlic minced
  • 1 TBSP olive oil
  • 28 ounce can of San Marzano peeled whole tomatoes
  • 1 14 ounce can of unsalted diced tomatoes
  • 4 cups of chicken stock
  • ¼ teaspoon garlic powder
  • ¼ teaspoon smoked paprika
  • 1 to 2 dashes of cayenne pepper
  • ¾ cup of heavy cream
  • 10 large basil leaves torn
  • Salt and pepper to taste
  • For the Greatest Grilled Cheese You’ll Ever Eat;
  • 1 loaf of multigrain white bread sliced. I used a multigrain oat white bread.
  • 4 ounces of Tillamook Medium Cheddar sliced thin
  • 4 ounces of Tillamook Medium White Cheddar sliced thin
  • Mayonnaise


  1. For the Creamy Tomato Basil Soup;
  2. In a Dutch Oven, heat your olive oil over medium heat then add your yellow and sweet onions.
  3. Cook over medium heat until onions have softened and browned slightly, about 15 minutes.
  4. Add your garlic and cook for an additional minute.
  5. Next, add in your San Marzano tomatoes and loosely break up the whole tomatoes with your cooking utensil then add in the can of diced tomatoes, chicken stock, and spices.
  6. Cook on medium low for 15 minutes, allowing the mixture to come to a heavy simmer.
  7. After 15 minutes has passed, using an immersion blender, blend the ingredients in the pot until completely smooth and all the large chunks have dissolved.
  8. Pour in your cream and add your torn basil then hit it with the immersion blender again. Let simmer for 20 or more minutes. The longer it cooks, the thicker the soup. I pulled mine at 20 and it was perfect.
  9. Remove from heat, add any additional salt or pepper to your tastes and get ready to plate once you’ve made your grilled cheese sandwiches.
  10. For the Greatest Grilled Cheese You’ll Ever Eat;
  11. Heat a non-stick skillet with a glass lid over medium low heat.
  12. When the skillet is hot, spread mayonnaise on one side of the white bread slice, and place mayonnaise side down in the skillet. Quickly layer on your cheese alternating between white and orange cheddar.
  13. Place the lid to the skillet on and let the heat from the pan slowly melt the cheddar while you spread mayonnaise lightly on the top layer of bread, about 1 minute.
  14. Remove the lid, place the other slice of bread mayonnaise side up, and carefully flip the sandwich. The now top slice should have a perfectly golden crust.
  15. Let the bottom piece of bread crisp up for about 1 to 2 minutes in the pan, checking every 30 seconds for the perfect color.
  16. Remove and let cool for about a minute before cutting. Enjoy the greatest grilled cheese sandwich you’ll ever eat with a cup of creamy tomato basil soup!

Recipe Notes

For the soup, soup is always better if you let it sit for a day or two. I found that this creamy basil tomato soup was exponentially better on day two even though on day one it was terrific. For the grilled cheese, mayonnaise may not be a conventional way to toast your grilled cheese, but it gives your sandwich the perfect umami flavor without adding any additional spices and it doesn’t leave your bread soggy like using traditional butter can. I encourage you to try it next time you go to toast any sandwich in a skillet!