In a large stockpot heat olive oil over medium high heat. Add onions and saute until soft and translucent. Add in the garlic and saute until garlic is fragrant, about 1 to 2 minutes more.
Add vegetable stock, tomatoes, squash, potatoes, basil, oregano and red pepper flakes to pot, when it starts to boil reduce heat to medium low and simmer stirring occasionally to prevent sticking.
Taste and add salt as needed.
When vegetables are fork tender remove from heat and cool slightly.
In batches transfer soup to blender and blend until smooth and creamy.
At this point you can blend in crean, milk, parmesan or pesto. I added pesto to my soup.
While soup is cooking pre-heat oven to 350 degrees and prepare bread.
Slice baguette lengthwise, spread with pesto and sprinkle on asiago, place in oven and bake until cheese is melted. Remove from oven and slice.
Serve soup with pesto toast.