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In a large soup pot heat 3 tablespoons of olive oil over medium heat. Add the onion, garlic, rosemary, and thyme and sauté until the onions are tender, about 2 minutes.
Toss the beef cubes in salt and pepper and flour. Turn up the heat to med-high and add the beef to the pot. Cook until the beef is browned and golden around the edges, about 5 minutes.
Add the Marsala wine. Using a wooden spoon, gently stir up all the brown bits off the bottom of the pan.
Add the butternut squash and sun-dried tomatoes and stir to combine.
Add enough beef broth to just cover the beef and squash. Bring the stew to a boil over high heat, then reduce the heat to low and simmer, covered, for 1 hour.
Season the stew with additional salt and pepper to taste. Sprinkle with the chopped parsley. Serve with crusty bread alongside.
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