If you love the taste of in-season, fresh heirloom tomatoes, and oven roasted Roma tomatoes, with hints of sweet, mild shallots and the mellowness of roasted garlic, you must try this soup.
Heat oven to 375F and adjust rack to middle position. Line a large baking stone/sheet with parchment paper.
Cut the Roma tomatoes lengthwise into quarters.Remove the core and as many seeds as possible. Seeds can be bitter, and we don't want a bitter soup.
Cut 1/2 poundof the heirloom tomatoes in half horizontally and spoon out as many seeds as
possible. Slice the shallots thinly.
Arrange the shallots, and unpeeled garlic in a single layer over one area of the baking stone/sheet.
Arrange the tomatoes cut side up and lightly sprinkle with salt and pepper.
Roast for 20 minutes then remove the shallot and garlic. Return the sheet to the oven and continue to roast the tomatoes until softened, but not brown. Another 12-16 minutes. Remove from oven, and let cool to room temperature. About 30 minutes.
Peel the garlic cloves and place in a blender with the roasted shallows and roasted tomatoes. Cut the remaining 3/4 pound of heirloom tomatoes into eighths and add to the blender with the tomato paste, heaping 1/2 tsp. salt, cayenne and a couple pinches of black pepper. Puree until smooth about 30 seconds.You may have to do this in two batches. If so, simply blend the fresh tomatoes with the spices , garlic, shallots and tomato paste, then add the roasted tomatoes and puree until smooth.
While the blender is still running, drizzle in the olive oil in a slow steady stream.
Pour the puree through a fine-mesh strainer into a glass bowl (not metal), pressing on the solids to extract as much liquid as possible.Discard the solids. Stir in the vinegar . Cover and refrigerate until chilled and the flavors have married- at least 6 hours up to 2 days, maximum.
To serve, stir soup vigorously (liquid separates upon standing). Taste and adjust seasoning with salt and vinegar as needed.Ladle soup into bowls (chilled if desired) sprinkle with basil, a few cranks of black pepper from your pepper mill, and olive oil, if desired.; Serve immediately.