Preheat the oven to 400 F and line a large baking sheet with parchment paper.

Prepare the squashes by chopping off the stem, and then slicing in half vertically. Scoop out the seeds and discard.

Place the squashes on the baking sheet, cut side up and top with 2 tbsp olive oil, salt, and cinnamon. Flip the squashes so they're cut side down and roast in the preheated oven for 35-40 minutes until soft. Remove from the oven and set aside.

Using a large pot, heat 1 tbsp of olive oil over medium heat. Add the onion and garlic and saute for 3-4 minutes. Add the carrots and saute for another few minutes until lightly softened.

Pour in the broth, and add the herbs. Bring to a boil and reduce to a simmer for 10 minutes. Once cooked, remove from the heat and allow to cool slightly.

Use a spoon to scoop out the flesh of the squash (discarding the skin) and add to a blender along with the soup base. Blend until fully combined.

Serve the soup topped with coconut milk and optional sage leaves.