Place cashews in a small bowl, cover with water and soak for one hour.
Preheat oven to 400 degrees. Line baking sheet with tin foil.
In a large bowl, combine tomatoes, vinegar, olive oil and salt & pepper and toss to combine. Spread out on baking sheet.
Cut the top of the garlic head off, drizzle with olive oil, wrap tightly in tin foil and place on baking sheet with tomatoes.
Roast for 45 minutes.
Meanwhile, add soaked cashews and 1/4 cup of the almond milk to a food processor. Process until a paste forms, scraping down sides as needed. Set aside.
When there's about 10 minutes of roasting time left, heat large heavy bottomed pot over medium-high heat.
Add onions and garlic and saute until softened, about 5-7 minutes.
Once tomatoes and garlic are done, add to pot (squeezing the roasted garlic out of the cloves) and cook for about 5 minutes.
Add broth, 1 cup almond milk, parsley, 1/2 cup of the cashew paste and salt & pepper. Cook uncovered on a low simmer for another 15 minutes.
Remove pot from heat and transfer soup to a blender. Blend (in batches if necessary) until smooth. Alternatively, an immersion blender could be used.
Season to taste. Set aside.
Add remaining cashew paste to blender with the remaining 1/4 cup almond milk and blend on high until a creamy consistency forms. Transfer to a small bowl.
Serve soup while warm adding as much cashew cream as desired on top. Garnish with extra parsley.