Remove the stems and core from the tomatoes. Cut the tomatoes in half and place flat-side-down on a parchment-lined baking tray. If using cherry tomatoes, add the tomatoes whole to the baking tray.
Add the red bell pepper and garlic to the baking tray, followed by the olive oil, salt and pepper. Toss everything to combine and bake in the oven for 25-30 minutes, or until the skins of the tomatoes and peppers have charred and can easily be peeled away. Let cool for 15 minutes.
Once the tomatoes and peppers are cool to the touch, remove the skins from them and discard. Add the flesh of the tomatoes, peppers and garlic to a large pot. Make sure to add any juice from the tomatoes that is left on the pan to the pot.
Place the pot on the stove over medium heat. Add the pureed tomatoes and water and use a stick blender to blend the soup until it is completely smooth. You can also add the soup to a blender instead.
Once smooth, add the Parmesan rind (or Parmesan cheese) and basil leaves. Bring the pot to a boil, cover, and simmer for 20 minutes.
Serve to soup while it is hot with a drizzle of half-and-half, if desired. Don't forget to serve with a grilled cheese sandwich on the side for dipping!
This is a great meal prep recipe and can be made in a large batch and frozen in individual servings. Simply thaw and reheat whenever you have a Garden Tomato Soup craving!