Prepare the Cucumber Water: Place cucumber slices into a pitcher with cold water. Chill in the fridge while preparing the soup. Add ice cubes before serving if desired.
Heat the extra virgin olive oil over medium heat. Add the onion to the pot and cook until softened, approximately 3 - 4 minutes.
Stir in the garlic and cook for 1 minute. Add the Italian seasoning and tomato paste, stirring to combine. Continue cooking for 2 - 3 minutes longer or until the tomato paste begins to turn a deep burgundy color.
Add the wine to the pot and using a wooden spoon, scrape up the brown bits on the bottom of the pot. Bring to a boil and cook until reduced by half.
Add the tomatoes, chicken stock, and chicken to the pot, stirring to combine. Bring the soup to a boil, then reduce the heat to low.
Stir in the tortellini and cook according to the instruction on the package.
Slowly stir in the half and half and cheese, then add the kale. Simmer for an additional 1 - 2 minutes then season with salt and pepper to taste.
Serve: the Tuscan tortellini soup. Garnish with grated Parmesan cheese. Serve alongside the chilled cucumber water.