Spread the tomatoes on a baking sheet (13" x 9"). Add chopped onions and garlic heads (trim about ¼" the top of the head). Drizzle extra virgin olive oil on the garlic and tomatoes. Generously sprinkle salt and black pepper on top.
Bake in the oven for 30 minutes. Remove from the oven and let cool for 15 minutes. Press the bottom of the garlic cloves to free them from the outer peel/skin, then discard the peeling.
Transfer the roasted tomatoes to a pot/dutch oven. Using a handle blender (if you don't have one, wait for another 10-15 minutes to cool down before transferringthe soup to a regular blender), puree until smooth.
Heat the pot/dutch oven to medium heat. Add vegetable broth, sugar and mix. Simmer for 15 - 20 minutes until thickens to your liking.
Add heavy whipping cream and stir ever together. Season with salt and pepper as needed.
Serve with grilled cheese, croutons, toast or crackers. Enjoy!