Prepare vegetables. Remove outer layers of skin from garlic, leaving enough though that the garlic stays connected together. Chop the top of the garlic head off. Cut a couple large chunks of red onion, removing skin and outer layer. Cut large chunks of tomato, avoiding the stem and leaving the skin on.
Once prepared, add vegetables to a greased baking sheet. Drizzle olive oil all over the vegetables and add salt and pepper. Gently rub olive oil and seasonings all over the vegetables to make sure they are fully coated.
Place the baking sheet in the oven for 30 minutes at 390 degrees.
Add roasted vegetables to a large pot or Dutch Oven. You can add the onion and tomatoes as is. You should be able to "pop" the pieces of garlic out of the skin easily.
Add Italian seasoning and 1/2 cup vegetable broth.
Use an immersion blender to blend the roasted vegetables until smooth. *Remove any big or thick chunks that are too tough for the blender.
Pour in 1/2 cup of heavy whipping cream. Serve and enjoy!
Notes
See my "Tips & Advice" section for helpful information!