Preheat oven to 400 F.
Cut top off of head of garlic to expose cloves.
On a parchment paper lined baking sheet, place the chopped onions, garlic, basil, and thyme. Toss with olive oil, red pepper flakes, salt, and pepper.
Place in oven and bake for 30 minutes. Remove from oven and discard thyme.
In a large pot on the stove on medium heat, add tomatoes with juice, contents of baking sheet (squeeze all roasted garlic cloves out of the head of garlic into the pot and discard head), coconut milk, sugar, and dried oregano.
Stir all ingredients and let simmer for 10 minutes.
In batches, pour the soup into a blender and puree until smooth. Return soup to pot, adding salt and pepper to taste.
Thin with vegetable broth if desired.
Ladle the soup into bowls and if desired, topped with any of the optional toppings (grated parmesan, croutons, or fresh basil)!