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Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.

Prepare the vegetables for roasting: Roughly chop the large red tomatoes. Remove cherry tomatoes from their stems. Chop the red bell peppers. Cut the white onion into wedges. Place all prepared vegetables and the two whole, unpeeled heads of garlic onto the prepared baking sheet.

Drizzle the vegetables generously with 1/4 cup of olive oil. Season with 1 teaspoon of salt, 1/2 teaspoon of freshly ground black pepper, and 1 teaspoon of Italian seasoning. Toss to ensure all vegetables are evenly coated. Roast in the preheated oven for 35-40 minutes, or until the vegetables are tender and slightly caramelized or charred.

Once roasted, remove the baking sheet from the oven. Carefully squeeze the softened garlic cloves from their skins into a large pot or Dutch oven. Add the roasted tomatoes, cherry tomatoes, bell peppers, and onion to the pot.

In the same pot (or a separate small saucepan if preferred), melt 2 tablespoons of butter over medium heat. Add 2 tablespoons of tomato paste and sauté for 2-3 minutes, stirring constantly, until it darkens slightly. Stir in 1/2 cup of finely chopped fresh basil.

Pour in 4 cups of chicken or vegetable broth. Add 1 teaspoon of packed brown sugar and 1/2 teaspoon of garlic powder. Bring the mixture to a simmer, then reduce heat to low, cover, and let it cook for 10-15 minutes to allow the flavors to meld.

Remove the pot from the heat. Using an immersion blender, blend the soup directly in the pot until it is smooth and creamy. Alternatively, carefully transfer the soup in batches to a regular blender and blend until smooth (be cautious when blending hot liquids). Return the blended soup to the pot. Stir in 1/2 cup of heavy cream until fully combined.

While the soup simmers or blends, prepare the grilled cheese sandwiches. Spread softened butter evenly on one side of each slice of bread. Place 4 slices of bread, butter-side down, in a large skillet over medium heat. Distribute the shredded white cheddar or provolone cheese evenly over these slices. Top with the remaining 4 slices of bread, butter-side up.

Cook the grilled cheese sandwiches for 3-5 minutes per side, or until golden brown and the cheese is melted and gooey. Remove from heat and cut each sandwich in half diagonally.

Ladle the creamy roasted tomato basil soup into bowls. Garnish with a swirl of fresh cream and a fresh basil leaf. Serve immediately with the grilled cheese sandwich halves for dipping.


Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.

Prepare the vegetables for roasting: Roughly chop the large red tomatoes. Remove cherry tomatoes from their stems. Chop the red bell peppers. Cut the white onion into wedges. Place all prepared vegetables and the two whole, unpeeled heads of garlic onto the prepared baking sheet.

Drizzle the vegetables generously with 1/4 cup of olive oil. Season with 1 teaspoon of salt, 1/2 teaspoon of freshly ground black pepper, and 1 teaspoon of Italian seasoning. Toss to ensure all vegetables are evenly coated. Roast in the preheated oven for 35-40 minutes, or until the vegetables are tender and slightly caramelized or charred.

Once roasted, remove the baking sheet from the oven. Carefully squeeze the softened garlic cloves from their skins into a large pot or Dutch oven. Add the roasted tomatoes, cherry tomatoes, bell peppers, and onion to the pot.

In the same pot (or a separate small saucepan if preferred), melt 2 tablespoons of butter over medium heat. Add 2 tablespoons of tomato paste and sauté for 2-3 minutes, stirring constantly, until it darkens slightly. Stir in 1/2 cup of finely chopped fresh basil.

Pour in 4 cups of chicken or vegetable broth. Add 1 teaspoon of packed brown sugar and 1/2 teaspoon of garlic powder. Bring the mixture to a simmer, then reduce heat to low, cover, and let it cook for 10-15 minutes to allow the flavors to meld.

Remove the pot from the heat. Using an immersion blender, blend the soup directly in the pot until it is smooth and creamy. Alternatively, carefully transfer the soup in batches to a regular blender and blend until smooth (be cautious when blending hot liquids). Return the blended soup to the pot. Stir in 1/2 cup of heavy cream until fully combined.

While the soup simmers or blends, prepare the grilled cheese sandwiches. Spread softened butter evenly on one side of each slice of bread. Place 4 slices of bread, butter-side down, in a large skillet over medium heat. Distribute the shredded white cheddar or provolone cheese evenly over these slices. Top with the remaining 4 slices of bread, butter-side up.

Cook the grilled cheese sandwiches for 3-5 minutes per side, or until golden brown and the cheese is melted and gooey. Remove from heat and cut each sandwich in half diagonally.

Ladle the creamy roasted tomato basil soup into bowls. Garnish with a swirl of fresh cream and a fresh basil leaf. Serve immediately with the grilled cheese sandwich halves for dipping.
