Place bacon pieces in a large dutch oven or pot over medium heat. Cook until browned and crisp. Remove bacon with a slotted spoon to a paper towel lined plate.
Add onion, carrots, celery and pepper to hot bacon grease. Cook until vegetables are softened, about 5 minutes. Stir in garlic for 1 minutes then stir in flour for another minute.
Slowly stir in chicken broth. Add tomatoes, basil leaves, salt, pepper and half of crumbled crisp bacon.
Remove basil leaves from soup and carefully transfer soup, in batches, to a blender and blend until smooth. Pour back into pot and stir in heavy cream. Simmer on low for 15 minutes. Top each bowl with remaining crumbled bacon pieces. Enjoy!