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Preheat oven to 400 degrees. Rub 1 tablespoon olive oil over squash. Place in oven on a baking sheet. Roast 30-40 minutes, rotating once, until fork tender. Meanwhile, in a large pot, heat 2 tablespoons olive oil over medium heat until hot. Add onion with a pinch of sea salt and stir 6 minutes, until translucent. Remove from heat and set aside.
With a large spoon, scoop flesh of squash into pot with onions. Return to a low flame until hot, about 5 minutes. Add vegetable broth and scrape bottom of pot with a wooden spoon. Season with sea salt and pepper and bring to a simmer.
In a small pan, heat 3 tablespoons olive oil. Fry sage leaves until crispy, about 2-3 seconds. Transfer to a paper towel and sprinkle with flaky sea salt.
Remove soup from heat and add cream, stirring to combine. Using a food processor or hand blender, process until completely smooth. Divide between 4 bowls, drizzle with olive oil and top with crispy sage.