Preheat the oven to 400°
Cut the sweet potato, carrots, shallot, and onion into thick wedges.
Seed the pepper and roughly chop. Cut the top off the garlic.
Place sweet potato, carrots, shallot, onions, peppers, garlic, tomatoes on the vine, and cauliflower onto a baking sheet and drizzle with olive oil. Season with salt, pepper, and cumin. Toss to coat.
Place into the oven on the center rack and bake for 15 minutes. Rearrange and bake for another 15 minutes.
Squeeze the garlic out of the shell.
Add all to a large stock pot.
Add the celery, broth, fennel, parmesan, and a pinch of salt and pepper. Cook for 20 minutes over medium heat.
Add the basil and heavy cream. Cook for 5 minutes, then use an immersion blender.
Garnish with fresh chopped basil, parmesan, and croutons. Enjoy!