Preheat the oven to 400°F (200°C). Cut the top off the head of garlic, drizzle with 1 tablespoon of olive oil, wrap in aluminum foil, and roast for about 30-35 minutes until soft and caramelized.

On a baking sheet, toss the cherry tomatoes with 1 tablespoon of olive oil, salt, and pepper. Roast in the oven for 20 minutes until blistered and slightly charred.

In a large pot, heat the remaining olive oil over medium heat. Add the chopped onion, carrot, and celery. Sauté for about 5-7 minutes until the vegetables are softened.

Squeeze the roasted garlic cloves out of their skins and add them to the pot along with the roasted tomatoes, vegetable broth, basil, and oregano. Bring to a simmer and cook for 10 minutes.

Use an immersion blender to puree the soup until smooth. If using a regular blender, allow the soup to cool slightly before blending in batches.

Stir in the heavy cream and heat through. Adjust seasoning with salt and pepper as needed.

Serve hot, garnished with fresh basil leaves.