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Preheat oven to 400 degrees F.
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Add 2 tablespoons of olive oil, fresh cherry tomatoes and sliced red bell pepper to a large bowl. Season with salt and pepper and toss to combine.
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Arrange on a large baking sheet and roast for 20-30 minutes.
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Add 2 tablespoons of olive oil to a large pot or Dutch oven over medium heat and cook the onion, celery, salt, pepper, red pepper flakes, paprika, and basil for about 5-6 minutes or until the onions are translucent.
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Add in the garlic and stir for 30 seconds before adding in the roasted tomatoes and pepper, broth, crushed tomatoes, and sugar.
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Lower the heat to a simmer and cook for 30-40 minutes before blending until perfectly smooth with an immersion blender.
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Add in the heavy cream, mix well and serve using more heavy cream and parsley as garnishes.