Preheat the oven to 400 F. Line a baking sheet with parchment paper. Place the squash quarters on the baking sheet. Drizzle the squash with extra virgin olive oil and using your hands evenly spread the oil over the squash flesh. Season with salt and pepper. Bake for about 40 minutes or until squash is tender when pierced with a knife. Set aside to cool.
In a large stockpot, heat coconut oil over medium high heat. Add leeks, fennel, garlic, ginger, turmeric and a few pinches of salt. Turn heat to medium low and simmer vegetables for about 10 minutes.
Peel the squash and cut into large cubes. Add the squash and vegetable broth to the stockpot with other vegetables. Bring to a boil and then reduce heat, simmering for 20-25 minutes.
Remove from heat and add coconut milk, curry paste and salt and pepper to taste. Stir to blend.
Working in multiple batches, blend the soup in a blender and return to the stockpot to thoroughly warm the soup.
Garnish with apple slices and cilantro.
Variation: add cooked shrimp