3 pounds (about 6 medium) ripe tomatoes, cored
1 small cucumber, peeled, halved, and seeded
1 small red onion, peeled and halved
2 medium garlic cloves, peeled and quartered
1 small jalapeno chile, stemmed and halved lengthwise
1 slice high-quality white sandwich bread, crust removed, torn into 1-inch pieces
1/2 cup extra virgin olive oil, plus extra for serving
2 tablespoons sherry vinegar, plus extra for serving
2 tablespoons finely minced parsley, chives, or basil leaves
Ground black pepper
Crumbled tortilla chips
Roughly chop 2 pounds of tomatoes, half of cucumber, and half of onion and place in large bowl. Add garlic, chile, and 1½ teaspoons salt; toss until well combined. Set aside.
Cut remaining tomatoes and cucumber into ¼-inch dice; place vegetables in medium bowl. Mince remaining onion and add to diced vegetables. Toss with ½ teaspoon salt and transfer to fine-mesh strainer set over medium bowl. Set aside 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 thoroughly to combine.
Transfer half of vegetable-bread mixture to 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 fine-mesh strainer into large bowl, using back of ladle or rubber spatula to press soup through strainer. Repeat with remaining vegetable-bread mixture and 1/4 cup olive oil.
Stir vinegar, minced herb, 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, crumbled chips and black pepper separately as garnishes.