Cut the top end off the head of garlic, so that the bulb remains intact and the cloves are exposed. Remove any of the papery loose outer layers. Place the garlic on a piece of aluminum foil, then drizzle with olive oil and sprinkle with salt and pepper. Wrap it in the foil then bake for about 50 to 55 minutes, until tender and the cloves are golden brown. Remove it from the oven, and once it is cool enough to handle, squeeze the cloves out of the peel, then use a fork to mash them into a paste. Measure out 1 tablespoon of the mashed garlic to use in the soup. Any extra can be stored in an airtight container in the fridge.
For the soup:
Add the olive oil to a large stockpot or Dutch oven set over medium heat. When hot, add in the onion and cook for about 5 to 6 minutes, until tender. Stir in the tomato paste. Add the cherry tomatoes, diced tomatoes (with their juices), broth, coconut milk, salt, pepper, oregano and the 1 tablespoon roasted garlic to the pot. Mix to combine then bring to a simmer. Reduce the heat and continue simmering for about 15 to 20 minutes, to allow the flavors to meld and the cherry tomatoes to soften and break down. Remove from the heat.
Carefully transfer the soup to a blender and process until smooth. Return the soup to the pot. Taste and season with additional salt and pepper as needed. Serve garnished with fresh basil and bread on the side for dipping.