McCaw was taught to fly gliders by his grandfather J H 'Jim' McCaw who flew more than 300 missions in the Second World War. In 2009 he convinced the head of the Discovery network in Australia and New Zealand to do a show about gliding. They filmed McCaw gliding at Omarama on the extreme sports series "Sportstar Insider", which was hosted by Australian former rugby league footballer Andrew Ettingshausen. After the 2010 Canterbury earthquake he auctioned a personal flying lesson through Trade Me to raise money for the badly damaged Hororata St Johns Church. He is also raising money for a young Samoan who broke his neck playing rugby and whose village was destroyed in the 2009 Samoa earthquake and tsunami. It was revealed at his retirement announcement in 2015 that McCaw would work at Christchurch Helicopters, where he is a Director and Shareholder, and was obtaining a commercial helicopter licence. McCaw has since obtained said licence and has continued working as a helicopter pilot. He flew several rescue and reconnaissance missions following the 2016 Kaikoura earthquake that struck the South Island. He also performed milk drops around rural areas of New Zealand while having an endorsement with Fonterra, in which his sister and her husband are dairy farmers.