Slice squash in half and remove seeds. Place halves into a baking dish, open side down. Drizzle olive oil, cover with foil; bake for 30-45 minutes, checking for doneness by piercing with a fork and looking for a softer texture.
Once done, remove flesh and allow to cool. Place into a blender and puree, adding coconut milk a little at time to begin thinning. Pour into sauce pan and warm over low heat; stirring occasionally to avoid from sticking on the bottom of the pan. More milk may be added if a thinner consistency is desired; season with salt and pepper.
Garnish with a fresh basil leaf and serve with sliced oranges.