Preheat the oven to 400°F (200°C).
Place halved Roma tomatoes on a baking sheet, drizzle with olive oil, and sprinkle with salt & black pepper.
Roast for 20-25 minutes until slightly charred and caramelized.
Warm up olive oil in a big pot on medium heat.
Toss in the chopped onion and garlic, and cook for about 5 minutes until they’re soft and smell amazing.
Add roasted (or canned) tomatoes, tomato paste, vegetable broth, basil, oregano, salt, pepper, and red pepper flakes (if using).
Simmer uncovered for 15 minutes, stirring occasionally.
Blend the soup right in the pot using an immersion blender until it’s smooth. (Or transfer to a blender in batches, being careful with the hot liquid.)
Blend until silky smooth.
Stir in coconut milk or cashew cream and maple syrup.
Taste and adjust seasoning as needed. Simmer for 2 more minutes.
Ladle into bowls, garnish with fresh basil or croutons, and enjoy!