Preheat the oven to 350 degrees Fahrenheit. Slice your tomatoes in half and prepare a baking sheet covered with parchment paper. Once the oven is heated, place tomatoes with the cut side facing up onto the baking sheet. Sprinkle with salt, pepper, and olive oil. Roast for an hour.
In a large pot, heat 2 tablespoons of olive oil on medium heat. Add in all of your ingredients, including the tomatoes, and simmer for about 20 minutes.
Pour your mixture into the blender and blend until smooth. You can serve by topping with basil.