Raymond Fuller, 88, from Poole, joined the Royal Navy as a 17 year old in 1943 and served on HMS Illustrious. The carrier's aircraft attacked targets in Japanese-occupied Dutch East Indies and took part in the Battle of Okinawa.
Mr Fuller's pilgrimage in the new year is being funded by the Big Lottery Fund's Heroes Return scheme. In early 1944, the aircraft of HMS Illustrious and an American carrier joined forces to strike a naval base at Sabang in northern Sumatra. The ship went on to Tricomalee in Sri Lanka for respite before the start of the Battle of Okinawa in 1945.
Mr Fuller said: "I remember Christmas Day 1944 very well because we had some free time to do whatever we liked, before the discipline clamped down again on Boxing Day.
"One chap said 'I fancy swimming over to that destroyer for a cup of tea' - and he did. I gather he was well received on board.
"It was a very welcome break - we used to get so tired. It was so hot down in the hangar and during action stations it was closed up and the ventilation was switched off so it was like working in an oven."
The Kranji memorial is dedicated to the men and women from the UK, Australia, Canada, Sri Lanka, India, Malaya, the Netherlands and New Zealand who died defending Singapore and Malaya against Japanese forces.
Mr Fuller said: "You did get to know some of the pilots. It was very sad when you found out they didn't return. "It will be important to visit the cemetery and spend some time thinking about those who never made it - especially the PoWs."
Big Lottery Fund chairman Peter Ainsworth said: "It is worth reminding ourselves that veterans spent Christmases in very different circumstances during the Second World War, so that we could have the peace and freedoms we enjoy today."
The Heroes Return programme has awarded in excess of £28m to more than 57,000 veterans, widows and carers since 2004.