Simon Hagger

CEO Shortbreaks Ltd (deputy CEO Holiday Extras Group)

Simon joined Holiday Extras as the first ever graduate trainee back in 1996 and worked his way around the business holding various management roles; hotel contracts manager, head of commercial, head of call centre and holiday insurance operations among them. It was his role as new ventures manager which led to a position on the executive board of directors as new business director in September 2006. Simon became CEO of Short Breaks in December 2009, and in 2015 he was also appointed to the role of Deputy Group CEO.

Simon is responsible for moving the Holiday Extras Group into the short breaks market, launching London theatre breaks under the Show and Stay brand and theme park breaks via Play and Stay. Both offerings have evolved over the years, with Simon's team now principle operator of the official short breaks for Merlin Entertainments Group in the UK and Germany (LEGOLAND Windsor, Thorpe Park, Chessington World of Adventures, Alton Towers and LEGOLAND Deutschland). The Eden Project and Peppa Pig World at Paultons Park are recent additions to the Short Breaks portfolio.

Simon picked up Travolution's Rising Star of the Year award in 2010 - he has increasingly found his responsibility expanding into e-commerce as well as commercial leadership; currently leading the fastest online growth section of the Holiday Extras group.

Life before Holiday Extras

Simon's degree in Geography from the University of London inspired his passions for travelling the world and a career in the travel industry. After seeing Australia, New Zealand, Indonesia, the USA, Canada and Thailand, and flirting with a career in personal fitness training in Sydney, Simon headed back to the UK and

Life outside of work

Simon has a love of cycling (mountain and road biking), walking, gardening and Guinness!...but mostly enjoying time and activities with his family. He is married and has two daughters.

What's your perfect hassle-free holiday?

Can I have two?! A simple UK camping trip with my family, fresh air, free reign and fun for the kids, being outside dawn 'till dusk. If there's no smart phone service - even better! On the other hand, I recently spent three nights with my wife in Umbria, Italy to celebrate our 10th wedding anniversary. No kids - that was perfect too, peaceful and full of delicious local food and wine (lots).


I love super creative people who take an idea and make it a reality, being passionate enough to roll with the knocks and keep going. Our troops who come back injured but despite this pick themselves up and get on with life, often going on to achieve even greater sporting, career, social and family success. Those guys who trekked to the North Pole with Prince Harry are a perfect example of how to overcome adversity.

And my kids - the way they view the whole world with wonder, possibility, optimism, opportunity and happiness. It's something we need to work hard to maintain as we grow up - I think these traits make for the best entrepreneurs too!