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

Prepare the vegetables: Halve or quarter the tomatoes. Core, seed, and quarter the red bell peppers. Peel and quarter the yellow onion. Slice off the top 1/4 inch of the garlic head, exposing the cloves.

Arrange the prepared tomatoes, bell peppers, onion, and the whole garlic head on the lined baking sheet. Drizzle generously with olive oil, then sprinkle evenly with kosher salt, freshly ground black pepper, and fresh thyme leaves. Toss gently to ensure all vegetables are coated.

Roast the vegetables in the preheated oven for 30 to 40 minutes, or until they are very tender, slightly charred, and fragrant. The garlic cloves should be soft and golden.

While the vegetables are roasting, prepare the grilled cheese bites. Butter one side of each slice of bread. Place two slices of cheese between two slices of bread, butter-side out. Heat a small skillet over medium heat. Cook the sandwiches for 3-5 minutes per side, or until golden brown and the cheese is melted and bubbly. Repeat for the second sandwich. Set aside.

Carefully transfer the roasted vegetables (including any juices from the pan) to a high-speed blender. Squeeze the softened garlic cloves from their skins directly into the blender. Add the vegetable stock, 1/2 cup heavy cream, fresh basil leaves, and red pepper flakes. Blend until completely smooth and creamy. You may need to do this in batches depending on your blender size.

Pour the blended soup into a large pot or Dutch oven. Heat gently over medium-low heat, stirring occasionally, until warmed through. Do not boil.

Once the grilled cheese sandwiches have cooled slightly, cut them into small, bite-sized cubes.

Ladle the hot soup into bowls. Garnish each serving with a swirl of the remaining 2 tablespoons of heavy cream, a sprinkle of fresh black pepper, and a handful of the crunchy grilled cheese bites. Serve immediately.


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

Prepare the vegetables: Halve or quarter the tomatoes. Core, seed, and quarter the red bell peppers. Peel and quarter the yellow onion. Slice off the top 1/4 inch of the garlic head, exposing the cloves.

Arrange the prepared tomatoes, bell peppers, onion, and the whole garlic head on the lined baking sheet. Drizzle generously with olive oil, then sprinkle evenly with kosher salt, freshly ground black pepper, and fresh thyme leaves. Toss gently to ensure all vegetables are coated.

Roast the vegetables in the preheated oven for 30 to 40 minutes, or until they are very tender, slightly charred, and fragrant. The garlic cloves should be soft and golden.

While the vegetables are roasting, prepare the grilled cheese bites. Butter one side of each slice of bread. Place two slices of cheese between two slices of bread, butter-side out. Heat a small skillet over medium heat. Cook the sandwiches for 3-5 minutes per side, or until golden brown and the cheese is melted and bubbly. Repeat for the second sandwich. Set aside.

Carefully transfer the roasted vegetables (including any juices from the pan) to a high-speed blender. Squeeze the softened garlic cloves from their skins directly into the blender. Add the vegetable stock, 1/2 cup heavy cream, fresh basil leaves, and red pepper flakes. Blend until completely smooth and creamy. You may need to do this in batches depending on your blender size.

Pour the blended soup into a large pot or Dutch oven. Heat gently over medium-low heat, stirring occasionally, until warmed through. Do not boil.

Once the grilled cheese sandwiches have cooled slightly, cut them into small, bite-sized cubes.

Ladle the hot soup into bowls. Garnish each serving with a swirl of the remaining 2 tablespoons of heavy cream, a sprinkle of fresh black pepper, and a handful of the crunchy grilled cheese bites. Serve immediately.
