5 1/4poundsripe but firm tomatoes, cored and quartered, divided
1tablespoonolive oil
1tablespoonlight brown sugar
4carrots, peeled and chopped
2shallots, quartered
4garlic cloves, crushed
1teaspoonsalt
1/2teaspoonblack pepper
1/2teaspooncrushed red pepper
1tablespoontomato paste
2tablespoonsdry sherry
1 to 2cupschicken broth, divided
1/4cupheavy cream
1tablespoonbasil, chopped
Instructions
Preheat the oven to 400 degrees F. Line a baking sheet with foil; set aside.
In a large bowl, combine the 3 1/2 pounds of quartered tomatoes, olive oil, light brown sugar, carrots, shallots and garlic, and toss to coat. Season the vegetables lightly with salt and pepper. Transfer to the prepared baking sheet and roast until caramelized, about 30 minutes. Remove from the oven and let cool. When the tomatoes are cool enough to handle, peel off the skins and discard. Transfer the tomato flesh along with the rest of the roasted mixture to a large dutch oven and set aside.
Add 1 teaspoon salt, 1/2 teaspoon black pepper, crushed red pepper, tomato paste, dry sherry, remaining 1 3/4 pounds of tomatoes and 1 cup chicken broth to the dutch oven and bring to a boil over high heat. Reduce the heat and simmer until the vegetables are very tender, about 15 minutes.
Using an immersion blender, blend the soup until smooth.
Add the heavy cream and return to simmer. Season to taste with salt, and pepper. If desired, add more chicken stock until your desired consistency. Sprinkle each bowl with basil before serving.