Begin by preheating the oven to 400°F (200°C). Slice the tops off the garlic heads to expose the cloves, then place them cut-side up on individual pieces of aluminum foil. Drizzle each with a bit of olive oil and wrap tightly to form three sealed packets. Arrange the garlic parcels in a small baking dish and roast for about 45 minutes, or until the cloves are tender and golden. Remove from the oven and open the foil carefully to let them cool.
While the garlic roasts, start the soup base. In a medium soup pot over medium-high heat, melt the butter until it begins to foam. Add the chopped onion, along with sea salt and pepper. Sauté for about 3 minutes, or until the onion becomes soft and translucent.
Pour in the white wine and sprinkle in the Italian seasoning. Let it simmer briefly—about 1 minute—to allow the wine to reduce slightly and the herbs to bloom. Stir in the chicken stock and add the quartered potatoes. Bring the mixture to a simmer, then reduce the heat to low, cover the pot, and cook for 15 minutes, or until the potatoes are fork-tender.
Once the garlic is cool enough to handle, gently squeeze the roasted cloves from their skins and drop them into the simmering soup.
Using an immersion blender, puree the soup until it becomes velvety and smooth. If using a countertop blender, blend in batches with caution. Return the blended soup to the pot if needed, then stir in the heavy cream and grated parmesan cheese. Taste and adjust the seasoning with more salt and pepper if desired.
Ladle the garlic soup into bowls and finish with a handful of mini soup croutons, a sprinkle of chopped parsley, and extra parmesan cheese for garnish. Serve hot.