Preheat oven to 400° F.
To a baking sheet, add cherry tomatoes, onion wedges.
For the garlic, add it to a piece of foil and drizzle some olive oil. Wrap up and add to baking sheet with tomatoes and onion.
Drizzle olive oil over the onion and tomatoes, and season to liking with seasonings listed above. Add sage leaves on top of the tomato mixture somewhere.
Add to oven and roast for 40 min.
Once done, carefully (it will be hot) squeeze garlic bulb until most of the cloves come out, (they will be a pasty consistency.) into a bowl. Set aside.
Add tomato, onion, and sage mixture to a decent sized pot with some half and half or milk. Take an immersion blender and blend up until well combined. Add in your garlic and salt and pepper to taste.
Put soup on medium-high heat just to warm through a little more.
Serve with grilled cheese and garnish soup with herbs or green onion.
Enjoy!