Ingredients
- 4 cups cherry tomatoes
- 2 medium shallots, quartered lengthwise
- 3 tablespoons extra-virgin olive oil, divided
- 1 teaspoon dried oregano
- 1 (28 ounce) can no-salt-added crushed tomatoes
- 1 cup water
- ¼ cup packed chopped fresh basil, plus more for garnish
- ½ teaspoon salt
- ½ teaspoon ground pepper
- ¼ cup heavy cream
- 3 ounces rustic whole-wheat bread, cubed (3/4-inch; 2 cups)
Directions
- Preheat oven to 400°F. Line a large rimmed baking sheet with parchment paper.
- Toss cherry tomatoes and shallots with 1 tablespoon oil and oregano on the prepared baking sheet. Roast until the tomatoes burst and the shallots are tender, about 20 minutes. Do not turn the oven off.
- Meanwhile, combine crushed tomatoes, water, basil, salt and pepper in a blender; process until smooth, about 30 seconds. Add the roasted tomatoes and shallots; secure the lid on the blender and remove the center piece to allow steam to escape. Place a clean towel over the opening. Process until smooth, about 30 seconds. Pour into a large nonreactive saucepan.
- Bring the tomato mixture to a simmer over medium heat. Cook, stirring occasionally, until slightly thickened, 10 to 15 minutes. Stir in cream.
- Meanwhile, toss bread cubes with 1 tablespoon oil on a large rimmed baking sheet; arrange in an even layer. Bake until toasted and crisp, about 15 minutes. Divide the soup among 4 bowls; drizzle evenly with the remaining 1 tablespoon oil. Top with croutons and garnish with basil, if desired.

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