Preheat your oven to 400°F (200°C). Place the cubed butternut squash on a baking sheet and drizzle with olive oil. Season with salt, pepper, and a sprinkle of cinnamon. Toss to coat evenly.

Roast the butternut squash in the preheated oven for about 25-30 minutes, or until it becomes tender and slightly caramelized. Set aside.

In a large pot, heat the remaining olive oil over medium heat. Add the chopped onion and minced garlic. Sauté until the onion becomes translucent and the garlic becomes fragrant.

Add the diced tomatoes to the pot and cook for a few minutes until they start to soften.

Pour in the vegetable broth and add the roasted butternut squash. Bring the mixture to a boil, then reduce the heat and let it simmer for about 15-20 minutes to allow the flavors to meld together.

Using an immersion blender or a regular blender, puree the soup until smooth and creamy. Be careful when blending hot liquids, as they can splatter. If using a regular blender, blend in batches and vent the lid to release steam.

Return the soup to the pot and stir in the heavy cream, maple syrup, ground nutmeg, salt, and black pepper. Adjust the seasonings to taste.

Simmer the soup for an additional 5 minutes to allow the flavors to meld together. If the soup is too thick, you can add more vegetable broth or water to achieve your desired consistency.

Serve the butternut and tomato soup hot, garnished with a drizzle of cream, a sprinkle of cinnamon, and a few fresh basil leaves. Enjoy the cozy flavors of autumn!