Preheat oven to 450 degrees F. Cut 2 1/2 lbs tomatoes into halves. Place on baking sheet and drizzle with olive oil. Season with salt & pepper.
Cut off the top of garlic bulb, exposing each clove. Set bulb in foil, drizzle with olive oil and wrap closed. (Throw it on the same baking sheet as the tomatoes. They will roast at the same temp and time.)
Place in oven and roast for 45 mins.
In a large pot, heat olive oil. Sauté chopped onion until transparent.
Add minced garlic and red pepper flakes. Cook on medium-low heat for 2 mins.
Add canned tomatoes, fresh basil, parsley flakes, basil flakes, dried rosemary, and chicken / veggie broth to pot.
Simmer & stir occasionally until tomatoes are ready to be pulled out of the oven.
Add roasted tomatoes into pot.
Let garlic cool out of foil. Once it's easy to handle, squeeze each clove out garlic out of bulb and add to soup.
Simmer on medium-low heat for about 20 mins.
OPTIONAL: While that simmers, cook bacon. Crumble for toppings OR save for a bacon grilled cheese that pairs great with the soup. (yum). Set aside.
Use an immersion blender or food processor to puree the soup until smooth.
Stir in coconut milk after soup is fully blended.
Season with salt, pepper, garlic powder, and garlic salt. (To taste)
Take a spoon and taste test the soup! Always see if it needs more seasoning before serving. This part is all up to personal preference. (I sometimes add more red pepper flakes if needed.)
Let simmer for about 20 minutes.
Serve with bacon crumbles and mozzarella cheese on top! Or with grilled cheese's. (or both!) Enjoy!