Peel the tomatoes: bring a large pot of water to a rolling boil. Prepare an ice bath in a large bowl and set nearby. Carefully place the tomatoes in the boiling water. Boil for 30 seconds, or until the skin begins to split. Carefully transfer the tomatoes with a slotted spoon to the ice bath. Once cool enough to handle, gently peel the skins off and discard. Chop the tomatoes, discarding the seeds.
Add the soaked bread, tomatoes, cucumber, bell pepper, red onion, basil, garlic, lemon juice, water, red wine vinegar, salt, and pepper to a food processor or blender.
While blending, slowly add the olive oil and continue blending until the mixture has reached your desired consistency, adding more water as needed to reach your desired consistency..
Transfer the soup to a large bowl and refrigerate at least 30 minutes, or overnight, to allow the flavors to deepen.
Serve the soup chilled with a drizzle of extra-virgin olive oil, and garnish with croutons and fresh basil.