Quarter the tomatoes. If desired, blanch them in hot water first to remove the skins. Peel and chop the onion and garlic.
In a large pot, heat the olive oil over medium heat. Sauté the onion for 4-5 minutes, or until translucent.
Add the garlic and sauté for another minute, until fragrant.
Add the tomatoes to the pot and stir to combine with the onion and garlic. Cook over medium heat for 10 minutes, or until the tomatoes soften and release their juices.
Pour in the vegetable broth and season with basil, oregano, chili flakes, salt, and pepper. Add a pinch of sugar to balance the acidity of the tomatoes.
Bring the soup to a boil, then reduce heat and simmer for 15 minutes to allow the flavors to meld.
Use an immersion blender to puree the soup until smooth and creamy.
Stir in the heavy cream and heat through gently, being careful not to boil.
Garnish with fresh basil leaves before serving. Serve with freshly baked baguette or cheesy toast.
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