Seville's Creamy Gazpacho

Ingredients

• 2 pounds ripe red tomatoes, cored and roughly cut into chunks
• 2 teaspoons sherry vinegar, more to taste
• 1 small mild onion, peeled and roughly cut into chunks
• 1 cucumber, approximately 8 inches long, peeled and roughly cut into chunks
• 1/2 cup extra-virgin olive oil, more to taste, plus more for drizzling
• 1 Italian frying pepper or another long, light green pepper, such as Anaheim, cored, seeded and roughly cut into chunks
• 1 clove garlic