Callaloo, originally from Africa, is served throughout the Caribbean in different forms—from a thick side dish to the soup you see below. Slideshow: More Caribbean Recipes
In a stockpot or large saucepan, warm the olive oil over medium heat, then add the garlic. Sauté until fragrant, about 30 seconds, then add the onion; continue to sauté, stirring often, until the onion is translucent, about 4 minutes.
Add the peppers and sauté until softened, another 4 minutes. Stir in the okra, pumpkin, thyme, salt, pepper, coconut milk, chicken broth and Scotch bonnet pepper, if using. Bring to a simmer and reduce heat to low; simmer until the squash is fork-tender, about 20 minutes. Be careful to not burst the pepper when stirring the soup.
Stir in the spinach, in batches if needed (add more as it wilts and shrinks). Simmer until the spinach is soft and dark green, about 8 minutes.
Add the chives to the soup, and carefully fish out the pepper. Using an immersion blender or food processor, gently blend the soup until it is smooth but still has a little texture. Taste and add salt and pepper if needed.