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In a large pot over medium heat, add the olive oil. Once the pan is hot, add the onion, carrot, and garlic, stirring often for about 8 minutes or so.
Add the tomatoes, dried basil, salt, pepper, and broth. Bring to a gentle boil, then reduce heat to low, cover, and let cook for 15 minutes or so.
To make the crostini, preheat oven to 350F. Cut ciabatta bread into ½" thick slices and line them up on a large baking sheet (you may need to use two). Brush each slice with olive oil. Sprinkle each slice with the spicy cheddar cheese. Bake for 9-10 minutes or until golden brown and the edges are crispy.
Remove the cover from the soup, then use a blender or an immersion blender to blend until completely smooth. Remove the pot from the heat and stir in the heavy cream or coconut milk. Mix together well and taste to adjust salt and pepper.
Divide soup in bowls and serve with the cheddar crostini. Garnish with fresh basil and a drizzle of heavy cream if desired, and ENJOY!