Preheat oven to 375°F (190°C).
In a skillet, heat 1 tablespoon olive oil over medium heat. Add minced garlic and sauté until fragrant.
Add fresh spinach and cook until wilted. Remove from heat and mix with cream cheese, Parmesan cheese, salt, pepper, and dried Italian herbs.
Butterfly each chicken breast by slicing horizontally to create a pocket, being careful not to cut all the way through.
Stuff each chicken breast with the cream cheese and spinach filling and secure with toothpicks if needed.
Heat the remaining olive oil in a pan over medium-high heat. Pan-sear the chicken roll ups on each side until golden brown, about 3-4 minutes per side.
Transfer the roll ups to a baking dish and bake in the preheated oven for 15 minutes or until the chicken is cooked through and juicy.
Remove toothpicks before slicing. Slice the roll ups and arrange them in a fan shape on a white plate. Drizzle with olive oil and sprinkle with chopped parsley before serving.