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Preheat your oven to 350°F.
In a large roasting pan, place the vine tomatoes cut-side up, along with the cherry tomatoes, quartered onion, sliced bell pepper, and the whole head of garlic.
Drizzle the vegetables with olive oil and sprinkle with Italian seasoning, salt, and black pepper. Toss everything to ensure it's well coated.
Roast the mixture in the oven for 1 hour, or until the vegetables are soft, caramelized, and the cherry tomatoes are blistered.
Once roasted, transfer all the vegetables to a blender. Squeeze the roasted garlic cloves directly from the head into the blender.
Add the chicken or vegetable stock and water to the blender. Blend on high until the mixture is completely smooth, working in batches if necessary.
Pour the blended soup into a large pot set over medium heat.
Stir in the tomato paste and coconut milk, mixing well to combine.
Allow the soup to simmer for 10 to 15 minutes, until it becomes creamy and rich.
Serve the soup warm, drizzled with olive oil, and enjoy it with grilled cheese on the side.