Now 21, Harry looks back fondly on his younger days in this special feature, including that holiday.
“We went on a cruise when I was about four and I was playing football with all the chefs and lifeguards on the ship and I remember the ball went into the sea – I was devastated!” he said. “I had all my different kits as well, I used to collect them, all Tottenham kits, all different colours.
“When I was six, seven it was fun, just playing football, day to day, don't think about the future – it was pure football and fun. When you get to scholarship age, 16, 17, then it becomes real. You think ‘I might have a chance here’.”
Born in Hemel Hempstead, Harry joined our Academy as a schoolboy aged six before signing full-time in July, 2012. He signed his first professional contract two years later and his performances last season were rewarded with a new deal in February, keeping him at the Club until 2022.
Harry will look back at 2016-17 as his breakthrough season – 33 appearances in all competitions and that dream goal against West Ham in November. It's such a shame it ended abruptly with injury at Burnley in April, but he's working overtime to get back as quickly as possible.
“The most important thing is no matter what level you play at, enjoy it,” he added. “That's what football is about. That's the one thing I'd say through all my years at Tottenham, I've enjoyed every age group and every challenge, and I'm still learning and still enjoying.”