Peel squash with a carrot peeler or paring knife. Cut into quarters, scoop out seeds and chop into 1-inch (2.5-cm) cubes. Toss in olive oil and salt and pepper. Roast at 400°F (205°C) for approximately 10 minutes.

Place roasted squash in a large soup pot. Add wine and water to just cover squash. Bring to a rolling boil and turn to medium heat.

Meanwhile, add cumin to a dry, hot frying pan. Remove from heat and stir with a wooden spoon until just toasted, about 30 seconds; add to soup pot.

With a hand blender, purée soup. Add cream. Simmer 15-20 minutes, or until soup has reached desired consistency. Just before serving, add salt and pepper. Garnish with fresh basil.