Heat olive oil in a large saucepan over medium heat. Cook and stir onion and garlic in hot oil until fragrant, 2 to 3 minutes.
Pour vegetable broth over the onion mixture; add tomatoes, 1 tablespoon basil, maple syrup, and red pepper flakes. Bring the mixture to a boil, reduce heat to medium-low, place a cover on the saucepan, and simmer until the tomatoes are really soft, about 15 minutes.
With a hand held, immersion blender, blend soup until creamy, careful to keep blender from splashing.
Put pureed soup over medium heat and cook until hot, about 5 minutes. Stir remaining tablespoon basil and the cashew cream into the soup. Serve with a yummy hot sandwich or as shooters!
To make cashew cream, blend equal parts cashews and water.