Bring a large pot of water to boil. Score an X on the bottom of each tomato, then blanch for 10 seconds.
Transfer tomatoes to a colander and let cool slightly. Peel off skins, halve, remove seeds, and roughly chop.
Heat olive oil in a medium saucepan over medium heat. Add diced onion and cook, stirring frequently, until golden and softened, about 4 minutes.
Add minced garlic and cook until fragrant, 1 minute more.
Add chopped tomatoes and cook uncovered over medium heat for 20 minutes, stirring occasionally, until tomatoes break down and liquid reduces.
Transfer three-quarters of the mixture to a food processor or blender and puree until smooth. (Leave some texture by not pureeing everything — the chunky bits are what make this soup interesting.)
Return puree to saucepan and stir in red pepper flakes, torn basil, and milk. Heat through without boiling.
Season aggressively with salt and pepper. Ladle into bowls and garnish with additional fresh basil if desired.
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