Heat your oven to 400℉. Toss the cubes of squash, carrot, and potato in a roasting pan with one tablespoon of the olive oil, the salt and pepper and roast until just starting to char on the edges, about 30 minutes. Stir once or twice during roasting.
1 butternut squash, 4 small carrots, 1 Yukon gold potato, 2 tablespoons olive oil, 1 teaspoon kosher salt, ½ teaspoon ground black pepper
While the squash and carrots are roasting, add the remaining tablespoon of olive oil to a large pot over medium low heat. When the oil is hot, add the chopped onions and cook, stirring occasionally, until they have softened and just starting to turn a light brown.
1 onion
Add the minced garlic and cook for one minute.
2 garlic cloves
When the squash, carrots, and potato cubes are soft, add them to the soup pot along with the chopped pear. Stir to coat with oil and cook for a minute or two.
1 pear
Add one cup of water to the pot, cover, and cook at a low simmer - occasional bubbles - until all of the vegetables can be easily pierced with a knife or tines of a fork. You may need to add a bit more liquid if the vegetables are starting to dry out.
Remove the pan from the heat and let it cool just a few minutes. Puree the soup in your blender or with an immersion blender until perfectly smooth.
Transfer the squash carrot soup back to the soup pot, add the coconut milk, and heat over low until warmed through. At this point, adjust for salt, pepper and consistency. If your soup is too thick, add more water or broth. If it's too thin, let it simmer uncovered for a few minutes.
½ cup coconut milk
Serve hot with a swirl of cream, fresh herbs, crispy bacon bits, or a drizzle of hot honey.