Chilled Tomato and Stone Fruit Soup

Name: Chilled Tomato and Stone Fruit Soup
Ingredients: 2 pounds beefsteak tomatoes (about 4), quartered; 1 large English hothouse cucumber, peeled, seeded, cut into pieces; 1 large ripe peach, peeled, halved; ½ jalapeño, seeded (or with seeds for a spicier soup), chopped; ½ garlic clove; 1 cup fresh (or frozen, thawed) cherries (about 8 oz.), pitted; 2 Tbsp. (or more) white balsamic or Sherry vinegar; ¼ cup extra-virgin olive oil plus more; 1½ tsp. kosher salt plus more; Freshly ground black pepper; Flaky sea salt (such as Maldon)