1. Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper or lightly grease it.
2. Arrange the halved tomatoes cut side up on the baking sheet. Drizzle with 2 tablespoons of olive oil and sprinkle with salt, pepper, and dried oregano.
3. Place the whole head of garlic on the baking sheet as well—no need to peel the cloves; roasting will soften them.
4. Roast in the preheated oven for 35-40 minutes, until the tomatoes are caramelized and the garlic cloves are soft and fragrant.
5. While the tomatoes roast, heat the remaining tablespoon of olive oil in a large pot over medium heat. Add the chopped onion and sauté until translucent and sweet, about 8-10 minutes.
6. Once the tomatoes and garlic are done roasting, let them cool slightly. Squeeze the softened garlic cloves out of their skins and add them to the pot with the onions.
7. Add the roasted tomatoes to the pot, followed by the vegetable or chicken broth. Bring the mixture to a simmer and let it cook for 10 minutes to meld the flavors.
8. Using an immersion blender, puree the soup directly in the pot until smooth and creamy. Alternatively, carefully transfer the soup in batches to a blender and puree.
9. Stir in the heavy cream (or coconut milk) and balsamic vinegar if using. Adjust salt and pepper to taste. Warm the soup gently for another 5 minutes, but avoid boiling once the cream is added.
10. Serve hot, garnished with fresh basil leaves and a drizzle of olive oil if desired.

One of my favorite memories is making this soup with Ouma on a rainy afternoon. We roasted the tomatoes together, laughing as the kitchen filled with that irresistible roasted aroma. She reminded me how Mama Lou would always say, “Good food takes time, but it’s worth every minute.” That patience, that love, is what makes this soup so special.