Chop onion, celery, carrot, and tomatoes; press or mince garlic.
In a medium saucepan, heat 2 tablespoons of the olive oil over medium heat. Add the onion, celery, carrot, and 2/3 of the garlic; sauté 5-7 minutes until tender, stirring occasionally.
Add the crushed red pepper (optional) and tomatoes, and continue to cook 15 minutes, covered, until the tomatoes give up their liquid and begin to fall apart.
Add the water and orange juice and continue to cook, covered, about 15 minutes longer until the tomatoes have completely broken up. Season with salt and pepper to taste.
While the soup is cooking, combine the basil leaves, remaining garlic, and remaining oil in a blender and process until very smooth. Season with salt and pepper to taste, then cover and refrigerate until ready to use.
Remove soup from the heat and puree in a blender, working in batches if necessary (or use an immersion blender).
Ladle into bowls and garnish with drizzles of the basil-garlic puree.
Serve with a slice of Italian bread and orange wedges on the side.