With the continuous development of Macao and the growing population and visitors，the relationship between Macao and the region has become increasingly important. The Chief Executive pointed out，in his 2014 Policy Address，that enhancing regional cooperation to complement each other’s strength is an important policy for sustainable development and improving people’s livelihood in Macao. This paper analyses the recent overall regional development in Macao，its regional development plans and strategies in the future，and conducts a brief analysis of the future trends of cross-boundary living，from the perspective of transportation connectivity. Considering the increasing interaction between Macao and the region，a blueprint for the development of regional integration has been developed in the regional planning and overall planning of future reclaimed areas. As the cross-border travel being the basis of cross-border living of Macao，various cross-boundary transport infrastructure projects will be integrated with the rest of the regional network. This will provide the foundation of cross-border living for Macao residents in the future and help promoting inter-regional exchange of personnel and key elements. The recent extension of the opening hours of border checkpoints will help to improve the cross-border travel of Macao residents and visitors，as well as the internal traffic in Macao，which in turn will have a profound impact on the development of a more sustainable future in Macao. Looking ahead，the interaction with the region，especially the Pearl River Delta region，will be more frequent，and cross-border living will become more important. As such，cross-border travel will greatly increase，and there is a need to meet the new requirements for the next-round of development through enhanced customs clearance and cross-border transport infrastructure，especially the promotion of sustainable development and the improvement of people’s livelihood in Macao through regional cooperation.