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Preheat your oven to 375°F. On a large baking sheet, arrange the sliced Roma tomatoes, cherry tomatoes, garlic bulbs (sliced bottoms up), and chopped yellow onion. Season generously with salt, black pepper, and dried oregano. Drizzle with olive oil.

Roast the vegetables in the preheated oven for 45 minutes, or until they are tender and slightly caramelized.

Carefully transfer all the roasted vegetables from the baking sheet to a blender. Reserve one roasted garlic bulb for the grilled cheese sandwiches. Add the chicken broth, 1 cup heavy cream, 1/4 cup fresh basil, and granulated sugar to the blender. Blend until the mixture is super smooth and creamy.

Pour the blended soup into a large pot. Add a little more salt to taste, if needed. Let the soup simmer gently over low heat while you prepare the grilled cheese sandwiches.

Prepare the garlic cream cheese spread: In a small bowl, combine the whipped cream cheese, the pulp squeezed from the reserved roasted garlic bulb, Worcestershire sauce, shredded Parmesan cheese, and Italian seasoning. Mix well until all ingredients are thoroughly incorporated.

To assemble each sandwich: Spread a generous amount of the garlic cream cheese mixture onto two slices of sourdough bread. Layer Havarti and cheddar cheese slices on one piece of bread. Place the second slice of bread on top to form the sandwich. Repeat for all sandwiches.

Butter the outside of each sandwich (both sides) for a crispy crust. Place the sandwiches in a large skillet or on a griddle over medium heat. Cook until golden brown and the cheese is melted and gooey, flipping once. This usually takes about 3-4 minutes per side.

Serve the creamy tomato soup hot, garnished with a swirl of heavy cream and a fresh basil leaf. Cut each grilled cheese sandwich in half and serve alongside the soup for dipping.


Preheat your oven to 375°F. On a large baking sheet, arrange the sliced Roma tomatoes, cherry tomatoes, garlic bulbs (sliced bottoms up), and chopped yellow onion. Season generously with salt, black pepper, and dried oregano. Drizzle with olive oil.

Roast the vegetables in the preheated oven for 45 minutes, or until they are tender and slightly caramelized.

Carefully transfer all the roasted vegetables from the baking sheet to a blender. Reserve one roasted garlic bulb for the grilled cheese sandwiches. Add the chicken broth, 1 cup heavy cream, 1/4 cup fresh basil, and granulated sugar to the blender. Blend until the mixture is super smooth and creamy.

Pour the blended soup into a large pot. Add a little more salt to taste, if needed. Let the soup simmer gently over low heat while you prepare the grilled cheese sandwiches.

Prepare the garlic cream cheese spread: In a small bowl, combine the whipped cream cheese, the pulp squeezed from the reserved roasted garlic bulb, Worcestershire sauce, shredded Parmesan cheese, and Italian seasoning. Mix well until all ingredients are thoroughly incorporated.

To assemble each sandwich: Spread a generous amount of the garlic cream cheese mixture onto two slices of sourdough bread. Layer Havarti and cheddar cheese slices on one piece of bread. Place the second slice of bread on top to form the sandwich. Repeat for all sandwiches.

Butter the outside of each sandwich (both sides) for a crispy crust. Place the sandwiches in a large skillet or on a griddle over medium heat. Cook until golden brown and the cheese is melted and gooey, flipping once. This usually takes about 3-4 minutes per side.

Serve the creamy tomato soup hot, garnished with a swirl of heavy cream and a fresh basil leaf. Cut each grilled cheese sandwich in half and serve alongside the soup for dipping.
