Preheat your oven to 400°F (200°C) and line a baking sheet with parchment paper to prevent sticking. Gather your halved tomatoes, drizzle them with 1 tablespoon of olive oil, and season with salt and pepper.

Arrange the seasoned tomatoes cut-side up on the prepared baking sheet. Cut the top off a whole head of garlic, drizzle with 1 tablespoon of olive oil, wrap it tightly in foil, and place it on the baking sheet with the tomatoes. Roast both for 30-35 minutes.

While the tomatoes and garlic cool slightly, heat 1 tablespoon of olive oil in a large pot over medium heat. Add the chopped onion and sauté for about 5 minutes until the onions become translucent and tender.

Once your roasted garlic and tomatoes have cooled, squeeze the roasted garlic cloves into the pot with the sautéed onions. Add the roasted tomatoes, 2 cups of broth, and fresh basil leaves. Stir to combine.

Use an immersion blender to puree the mixture in the pot until smooth and creamy.

Return the blended soup to the pot over low heat. Stir in ½ cup of heavy cream or coconut milk and let it simmer gently for another 5-10 minutes to allow flavors to marry. Adjust seasoning with extra salt and pepper if needed.

Ladle the warm soup into bowls and garnish with fresh basil leaves, a drizzle of cream, or crispy roasted cherry tomatoes.