Step 1: Preheat oven to 475 degrees.
Step 2: Halve tomatoes lengthwise and lay them cut sides down in a jelly-roll pan.
Step 3: Brush generously with 3 tablespoons oil and sprinkle oregano, basil, and pepper.
Step 4: Roast tomatoes for 10 - 15 minutes. Sprinkle minced garlic over tops and continue roasting for an additional 5 to 12 minutes until tomato edges are charred, looking cooked and releasing their juices. Be careful not to over-roast so garlic won't burn. Scrape tomatoes, oil, and herbs from pan into food processor.
Step 5: Process until not quite smooth (leaving small chunks and charred black specks).
Step 6: In a saucepan cook onion in remaining 2 tablespoons oil until translucent. Whisk in roasted tomato puree, broth, and wine. Then whisk tomato paste.
Step 7: Heat the cream and whisk into the tomato mixture
Step 8: Taste and add sugar if necessary (the sugar helps cut the acidity of the tomatoes if they happen to be acidic)
Step 9: Stir in Parmesan. Add salt and pepper to taste and bring soup to a simmer.
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