01 - Preheat oven to 400°F. Slice the top off the garlic head and drizzle with 1 teaspoon olive oil. Wrap in foil and place on a baking sheet alongside the quartered tomatoes. Drizzle tomatoes with 1 tablespoon olive oil and season with salt and pepper. Roast for 35–40 minutes until softened and caramelized.
02 - Heat 1 tablespoon olive oil in a large pot over medium heat. Cook chopped onions until translucent, about 5–7 minutes.
03 - Toss bread cubes with olive oil, Italian herbs, and salt. Spread evenly on a baking sheet and bake for 10–12 minutes, tossing once, until crisp and golden. Set aside.
04 - Once roasted, squeeze garlic cloves from skins and add to the pot with onions. Add roasted tomatoes with their juices. Stir in vegetable broth, then bring to a simmer for 10 minutes.
05 - Stir in fresh basil leaves and sugar if desired. Remove pot from heat.
06 - Using an immersion blender or working in batches with a countertop blender, puree the soup until smooth. For a finer texture, strain through a fine mesh sieve.
07 - Stir in heavy cream or coconut milk for creaminess if using. Adjust salt and pepper to taste.
08 - Ladle soup into bowls and top with prepared croutons and additional fresh basil as garnish.