Cut a full head of garlic in half, crosswise. Cut a large shallot in half, lengthwise. Put in a small oven-safe dish, drizzle with olive oil and toss to coat. Cover loosely with foil and bake for 30-40 minutes until fragrant and tender. When you can handle them safely, remove the roasted garlic and shallot from their skins.
Put the tomatoes in a blender or food processor along with the roasted garlic and shallot. Puree until smooth.
Heat 2 tablespoons of olive oil in a Dutch oven until hot, but not smoking. Pour the tomato puree onto the hot oil, it may sputter a little bit so be careful.
Add the stock and basil to the pot. Bring to a simmer and simmer gently for 15 minutes.
Remove and discard the basil, and taste to adjust for seasoning. Add sugar if you'd like, and stir in the heavy cream. Serve hot with croutons and fresh basil leaves.
Nutritional information is provided as a courtesy and is an estimate only. This information comes from online calculators. Although The View from Great Island attempts to provide accurate nutritional information, these figures are only estimates.
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