01 - Preheat the oven to 400°F.
02 - Cut the top off the garlic head to expose the cloves. Drizzle with 1 tsp olive oil, wrap in foil, and place on a baking sheet.
03 - Arrange the tomatoes and onions on the baking sheet. Drizzle with remaining olive oil and sprinkle with salt and pepper. Roast for 30–35 minutes until soft and caramelized.
04 - Toss bread cubes with olive oil, oregano, and salt. Spread on a separate baking sheet and bake for 10–15 minutes until golden and crisp.
05 - Squeeze the roasted garlic cloves out of their skins once the vegetables are done.
06 - In a large pot, combine roasted tomatoes, onions, garlic, vegetable broth, basil, and sugar. Bring to a simmer over medium heat for 10 minutes.
07 - Use an immersion blender to purée the soup until smooth. Return to the pot and stir in cream if desired. Adjust seasoning with salt and pepper.
08 - Ladle soup into bowls and top with croutons and fresh basil.