Preheat your oven to 400°F (200°C). Spread the chopped pumpkin evenly on a baking sheet, drizzle with olive oil, and toss to coat. Roast for about 30-40 minutes until the pumpkin is tender and edges are lightly caramelized, filling your kitchen with a sweet, roasted aroma.
Meanwhile, wrap the garlic cloves in foil with a drizzle of olive oil and place them in the oven during the last 15 minutes of roasting. Once soft and fragrant, squeeze their creamy insides out of their skins and set aside.
Transfer the roasted pumpkin to a large pot. Add the softened garlic, vegetable broth, and coconut milk. Turn on the heat to medium and bring the mixture to a gentle simmer, allowing the flavors to meld and the soup to warm through.
Use an immersion blender or transfer the soup carefully to a blender. Puree until silky smooth, revealing a vibrant orange color and a velvety texture that coats the back of a spoon. Return the blended soup to the pot if needed.
Taste the soup and season with sea salt and black pepper to enhance the natural sweetness and depth of flavor. Stir well to distribute the seasoning evenly.
Allow the soup to simmer for another 5 minutes, stirring occasionally, until heated through and flavors are harmonized. The final result should be creamy, smooth, and invitingly warm.
Serve the hot pumpkin soup in bowls, optionally garnished with a splash of coconut milk or a sprinkle of herbs for added visual appeal. Enjoy this cozy, velvety treat on chilly days.