Preheat your oven to 400°F (200°C). Spread the cubed pumpkin on a baking sheet, drizzle with olive oil, and toss to coat evenly. Roast for about 25-30 minutes until tender and slightly caramelized around the edges, filling your kitchen with warm, sweet aroma.
While the pumpkin roasts, heat a splash of olive oil in a large pot over medium heat. Add the chopped onion and cook, stirring occasionally, until it becomes translucent and fragrant, about 5 minutes. Then, stir in the minced garlic and cook until just fragrant, about 1 minute.
Once the pumpkin is ready and slightly cooled, transfer it to the pot with sautéed aromatics. Pour in the vegetable broth and bring to a gentle simmer. Let it cook uncovered for about 10 minutes to meld the flavors and soften the pumpkin further.
Use an immersion blender directly in the pot or carefully transfer the mixture to a blender. Blend until the soup is completely smooth and velvety. Return it to the pot if needed, and stir in the coconut milk and vanilla extract for richness and a nuanced aroma.
Season the soup with sea salt and freshly ground black pepper, tasting and adjusting until balanced. Warm the soup through over low heat, stirring gently, until it reaches your desired temperature.
Serve the soup hot in bowls, garnished with a drizzle of coconut milk or a sprinkle of toasted pumpkin seeds if desired. Enjoy the smooth, fragrant, and subtly sweet flavor profile.