Combine gazpacho ingredients in a blender or food processor; process until smooth. Taste and adjust seasoning if needed. Pour mixture through a strainer and refrigerate for at least 1 hour.
Meanwhile, make croutons: Preheat oven to 400 F. Toss bread cubes with olive oil and lay in a single layer on a baking sheet. Toast, turning once, until golden brown and crisp, about 15 min.
Ladle chilled soup into bowls. Top with diced cucumber, cherry tomatoes, sliced basil, croutons and pepper.
Recipe courtesy of Ingrid Berger of The Happy Cook, Charlottesville