Preheat oven to 425°F
Add the chopped tomatoes, roughly chopped onion and 1 whole head of garlic to a baking sheet.
Season with salt, pepper and cover with olive oil.
Bake for about 45 minutes until the tomatoes are soft and starting to caramelize.
Scoop the tomatoes and onions into a blender.
Squeeze the garlic cloves into the same blender. Blend until combined.
Transfer the purée into a large soup pot along with the chicken or vegetable stock and a pinch of red pepper flakes (optional).
Bring the soup to a light boil and adjust seasoning.
Remove from heat and stir in heavy whipping cream.
Serve with crumbled feta and freshly chopped basil.
Enjoy!