Wash and cut tomatoes in half, place on a lined baking sheet along with the onion, pepper, and garlic cloves. Drizzle with olive oil. Bake for about 45 minutes to one hour.
In a large pot put everything that was roasted from the pan including juices, add the peeled and cut potato, and add all of the broth, bring to a boil and then simmer on med-low until all the vegetables are soft, about 20-30 minutes. Adjust to taste, you might need to add more or less sugar depending on the types of tomatoes used.
Blend the soup until it is smooth and then add the chopped basil leaves and blend for a couple of seconds just until the basil is finely chopped. You still want to see little bits of the basil throughout the soup. Finally add the cream and stir, serve with grilled cheese. Enjoy!