Astor spent his early years at Ferncliff Farm, the family's estate in Rhinebeck, New York. This rural setting provided a contrast to the bustling city life he would later embrace.

Astor maintained several residences in New York City, reflecting his prominent status and his involvement in the city's social and business life. He likely owned or resided in luxurious apartments and townhouses in prime locations.

Astor frequently traveled to Europe and other destinations for business and leisure, immersing himself in different cultures and experiences. His travels broadened his worldview and enhanced his cosmopolitan lifestyle. These travels were often to places like Paris, London, and Egypt.

Astor and his second wife, Madeleine, embarked on a honeymoon trip to Europe and Egypt, seeking to escape the scrutiny surrounding their marriage. This trip ultimately led to their fateful journey on the Titanic.