- 6 ounces hearty bread, crusts removed, torn into 1- to 2-inch chunks
- 3 pounds (about 4 large) very ripe tomatoes, cored and cut into rough 1-inch chunks
- Kosher salt and freshly ground black pepper
- 1/2 pound (about 1 small) cucumber, peeled, seeded, and cut into rough 1-inch chunks
- 1/3 pound (about 1 small) small red onion, peeled and cut into rough 1-inch chunks
- 1/3 pound (about 1 medium) green or red bell pepper, cored, seeded, and cut into rough 1-inch chunks
- 1/4 cup roughly chopped fresh oregano leaves
- 2 cloves garlic, peeled and smashed
- 1 cup extra-virgin olive oil, plus more for serving
- 2 tablespoons sherry vinegar, plus more to taste
- Chopped herbs such as parsley, chives, or oregano for serving
Place bread in bottom of a large bowl. Add half of the tomatoes in an even layer on top and season generously with salt and pepper. Add cucumbers, onion, peppers, and garlic. Sprinkle with oregano and season generously with salt and pepper. Add remaining tomatoes and sprinkle with more salt and pepper. Drizzle oil and vinegar over the top. Let rest at room temperature for 30 minutes.
Toss all ingredients with a wooden spoon or by hand until they are evenly incorporated. Transfer half of the contents, including liquid at bottom of bowl, to the jar of a blender. Blend on high speed until completely smooth, about 3 minutes. Press mixture through a fine mesh strainer into a large bowl. Repeat with remaining soup (you may need to work in more batches). Season soup with more salt, pepper, and vinegar as desired.
Serve immediately, garnished with chopped herbs and drizzled with extra virgin olive oil, or chill for up to three days before serving.