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Preheat your oven to 400°F (200°C).

In a large baking dish, combine the quartered large tomatoes, cherry tomatoes, quartered onion, chopped red bell pepper, and the halved garlic head. Drizzle with olive oil and season with salt, black pepper, red pepper flakes, and dried oregano. Toss gently to coat all vegetables.

Roast the vegetables in the preheated oven for 30-35 minutes, or until they are softened and slightly caramelized. The garlic should be very tender.

Carefully remove the baking dish from the oven. Allow the vegetables to cool slightly. Once cool enough to handle, squeeze the softened garlic cloves from their skins into the baking dish.

Transfer all the roasted vegetables and extracted garlic cloves, along with any accumulated juices from the baking dish, into a high-speed blender.

Pour 1 1/2 cups of vegetable broth into the blender with the roasted vegetables. Blend until the mixture is completely smooth and creamy. If the soup is too thick, add the remaining 1/2 cup of broth gradually until desired consistency is reached.

Pour the blended soup into a medium-sized cooking pot. Heat the soup over medium-low heat, stirring occasionally, until it is hot and simmering gently.

Remove the soup from the heat and stir in the heavy cream. Taste and adjust seasoning with additional salt or pepper if needed.

While the soup is heating, prepare the grilled cheese sandwiches. In a small bowl, mix the softened butter with garlic powder. Spread the garlic butter evenly on one side of each slice of bread. On the unbuttered side of four bread slices, layer the cheddar and Monterey Jack cheeses. Top with the remaining four bread slices, buttered-side up.

Heat a large non-stick skillet or griddle over medium heat. Place the assembled sandwiches in the hot skillet. Cook for 3-5 minutes per side, or until the bread is golden brown and crispy, and the cheese is melted and gooey.

Serve the hot creamy roasted tomato soup immediately, garnished with fresh parsley if desired. Cut the grilled cheese sandwiches in half and serve alongside the soup for dipping.


Preheat your oven to 400°F (200°C).

In a large baking dish, combine the quartered large tomatoes, cherry tomatoes, quartered onion, chopped red bell pepper, and the halved garlic head. Drizzle with olive oil and season with salt, black pepper, red pepper flakes, and dried oregano. Toss gently to coat all vegetables.

Roast the vegetables in the preheated oven for 30-35 minutes, or until they are softened and slightly caramelized. The garlic should be very tender.

Carefully remove the baking dish from the oven. Allow the vegetables to cool slightly. Once cool enough to handle, squeeze the softened garlic cloves from their skins into the baking dish.

Transfer all the roasted vegetables and extracted garlic cloves, along with any accumulated juices from the baking dish, into a high-speed blender.

Pour 1 1/2 cups of vegetable broth into the blender with the roasted vegetables. Blend until the mixture is completely smooth and creamy. If the soup is too thick, add the remaining 1/2 cup of broth gradually until desired consistency is reached.

Pour the blended soup into a medium-sized cooking pot. Heat the soup over medium-low heat, stirring occasionally, until it is hot and simmering gently.

Remove the soup from the heat and stir in the heavy cream. Taste and adjust seasoning with additional salt or pepper if needed.

While the soup is heating, prepare the grilled cheese sandwiches. In a small bowl, mix the softened butter with garlic powder. Spread the garlic butter evenly on one side of each slice of bread. On the unbuttered side of four bread slices, layer the cheddar and Monterey Jack cheeses. Top with the remaining four bread slices, buttered-side up.

Heat a large non-stick skillet or griddle over medium heat. Place the assembled sandwiches in the hot skillet. Cook for 3-5 minutes per side, or until the bread is golden brown and crispy, and the cheese is melted and gooey.

Serve the hot creamy roasted tomato soup immediately, garnished with fresh parsley if desired. Cut the grilled cheese sandwiches in half and serve alongside the soup for dipping.
