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Creamy and rich, you won’t believe it’s low calorie!
Preheat oven to 400°F.
Arrange tomatoes, cut sides up, in 1 layer in a large shallow baking pan (with sides) and add garlic to the pan. Drizzle tomatoes with oil and sprinkle with salt, pepper, celery flakes, and red pepper flakes. Roast seasoned tomatoes and garlic for 1 hour, then cool completely in the pan. Peel garlic (the skins should easily slip right off).
In a 6 to 8 quart heavy sauce pot, cook onion, oregano, and sugar in butter over low heat, stirring often, until onion is softened and slightly caramelized, about 5 minutes. Add tomatoes, garlic, and stock and simmer, covered, for 20 minutes.
Purée soup with a stick blender (use caution when blending hot liquids in a standard blender), then force through a sieve into a clean pot, discarding solids. Stir in cream and salt and pepper to taste and simmer 2 minutes.
Divide soup among 8 bowls and serve warm.
Note: Soup can be made 1 day ahead and cooled, uncovered, then chilled, covered. Reheat just before serving.
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