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Chilled Tomato and Stone Fruit Soup

['2 pounds beefsteak tomatoes (about 4), quartered', '1 large English hothouse cucumber, peeled, seeded, cut into pieces', '1 large ripe peach, peeled, halved', '1/2 jalapeño, seeded (or with seeds for a spicier soup), chopped', '1/2 garlic clove', '1 cup fresh (or frozen, thawed) cherries (about 8 ounces), pitted', '2 tablespoons (or more) white balsamic or Sherry vinegar', '1/4 cup extra-virgin olive oil plus more', '1 1/2 teaspoon kosher salt plus more', 'Freshly ground black pepper', 'Flaky sea salt (such as Maldon)']

Pulse tomatoes in a blender until finely chopped and transfer to a large bowl. Pulse cucumber, peach, jalapeño, garlic, and cherries in blender until finely chopped and add to bowl with tomatoes. Mix in vinegar, 1/4 cup oil, 1 1/2 teaspoon kosher salt, and 1 cup cold water; season with pepper. Cover and let sit at room temperature 1 hour, or chill at least 12 hours.
Season soup with kosher salt, pepper, and more oil and vinegar, if desired. Serve soup drizzled with oil and seasoned with sea salt and pepper.
DO AHEAD: Soup can be made 2 days ahead. Cover and chill.

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