3poundsabout 6 medium ripe tomatoes, cored, divided
1small cucumber, peeled, halved, and seeded
1medium green bell pepper, halved, cored and seeded
1small red onion, peeled and halved
2medium garlic cloves, peeled and quartered
1small serrano chile, stemmed and halved lengthwise
Kosher salt
1slicehigh-quality white sandwich bread, crust removed, torn into 1-inch pieces
1/2cupextra virgin olive oil, divided, plus extra for serving
2tablespoonsred wine vinegar, plus extra for serving
2tablespoonsfinely minced basil leaves
Ground black pepper
Instructions
Roughly chop 2 pounds of tomatoes, half of cucumber, half of bell pepper, and half of onion and place in large bowl. Add garlic, serrano chile, and 1½ teaspoons kosher salt; toss until well combined. Set aside.
Chop remaining tomatoes, cucumber, and pepper into ¼-inch dice and place in a medium bowl. Mince remaining onion and add to diced vegetables. Toss with ½ teaspoon kosher salt and transfer to fine-mesh strainer set over medium bowl. Set aside to drain 1 hour.
Transfer drained diced vegetables to medium bowl and set aside. Add bread pieces to exuded liquid (there should be about ¼ cup) and soak 1 minute. Add soaked bread and any remaining liquid to roughly chopped vegetables and toss to combine.
Transfer half of vegetable-bread mixture to a blender and process 30 seconds. With blender running, slowly drizzle in ¼ cup oil and continue to blend until completely smooth, about 2 minutes. Strain soup through a fine-mesh strainer into a large bowl, using back of a rubber spatula to press soup through strainer. Repeat with remaining vegetable-bread mixture and 1/4 cup olive oil.
Stir vinegar, minced basil, and half of diced vegetables into soup and season to taste with salt and black pepper. Cover and refrigerate overnight or for at least 2 hours to chill completely and develop flavors. Serve, passing remaining diced vegetables, olive oil, sherry vinegar, and black pepper separately for diners to season and garnish their own bowls as desired.