Historic canals, waterfront warehouses, and maritime headquarters, defined as Port City Heritage, are highly visible in Amsterdam, attracting locals and tourists around the world. However, global challenges and messiness threaten the citizen’s everyday life and well-being, such as pollution, gentrification, and climate change. As a non-biomedical intervention recognized by WHO and UNESCO, the historical urban environment and heritage play an important role in Human Well-being because they foster a sense of belonging, reduce stress, promote social connection, etc. With the development of Virtual Reality, immersive, interactive, and efficient heritage perception and well-being measurement become possible. This special session aims to raise participants’ awareness of Amsterdam's Port City Heritage, to investigate the impacts of this heritage on their Well-being, and the innovative application of Virtual Reality technology. This special session will take 1.5 hours both indoors and outdoors, and is composed of four parts 1) a Theoretical introduction to Amsterdam’s Port City Heritage and Human well-being (20 minutes), 2) an On-site heritage guided tour supported by VR technology (20 minutes), 3) Exploring the impact of heritage on well-being (20 minutes), 4) 20 minute Group Sharing & Discussion (20 minutes). Anyone at the AMS conference is welcome to this special session, especially those who are interested in Port City Heritage’s impact on citizens’ well-being and the application of embodied digital technology, VR/AR. The amount of participants is around 10-15 people (divided into 4-5 groups), so they will be able to fully interact, discuss, and experience this session. This special session will collaborate with TU Delft’s VR lab in A+BE, which will provide the VR headset devices for on-site experiments. The significance of this special session is to investigate the role of Amsterdam's Port City Heritage for Human Well-being and test the effectiveness of VR devices in heritage interaction.