Preheat the oven 400F. Set the cored tomatoes on a rimmed baking sheet. Drizzle with 2T of the olive oil and roast them until they look wrinkly, about 30 minutes, set aside. While the tomatoes cool, heat remaining olive oil in small sauté pan. Add the shallots and 2 cloves of chopped garlic sauté over medium-low heat until they turn golden brown and caramelize, 15/20 minutes, set aside
When tomatoes are cool enough to handle, peel off the skins. Put the peeled tomatoes in a blender along with the sautéed shallots and garlic, crushed tomatoes (with juice) 1 T salt and 1/8 tsp sugar. Process until the soup is smooth. Stir in the cream and vodka. Refrigerate in a covered bowl for at least 6 hrs, or overnight.
The soup can be made up to 4 days in advance. Serve warm or cold.
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