Our Team

"All our staff are chosen for their knowledge of sailing, friendliness, patience and sense of humour. Whether it be showing you the sights of Sydney, throwing you a line after your bareboat charter or teaching you the wonderful sport of sailing, my team will ensure you have a great day sailing on Sydney Harbour." Matt Hayes.

Our key people:

Matt Hayes - Managing Director

Matt Hayes has been sailing since he was a child, amassed a number of Australian Championships in various classes and competed in many world championships in the soling class, finishing on the podium on many occasions. Matt represented Australia at the Atlanta Olympics in 1996. He is a regular skipper in the Sydney to Hobart Yacht race, and has competed in the Admirals Cup and Kenwood Cup. Matt established his first sailing school when he was 19 and has dedicated his life to sharing the joys of sailing with thousands of customers. Matt established Sydney by Sail in March 1995 after winning the NSW Enterprise Workshop Award for Best Business Plan in 1994. Matt's dream is for as many people as possible to enjoy the pleasure of sailing on our world famous Sydney Harbour.

Ed Penn - General Manager

Ed Penn is a highly valued member of Sydney By Sail and has been since 1997. Ed is a highly experienced Commercial Skipper, Sail Trainer and possesses expert knowledge on a wide number of sailing related issues. His knowledge of Hunter yachts is arguably the best in Australia. Ed also holds Bachelor of Science degree.

Jonathan Dorrington – Operations and Fleet Manager

John has the sea in his veins. Originating from the UK, where he taught sailing from a young age, John made the move to Australia at the end of 2011. Since moving to Australia, John has enjoyed 4 years at Sydney By Sail, playing a key role in the day to day operations. John is extremely knowledgeable in all things yacht, with a history in engineering, his hands on approach is crucial for daily operations. John received his NSW Coxswain’s certificate in 2012 and since then has skipper over 150 sailing trips, whether that be manning a voyage up or down the coast of Australia, or just a cruise around the harbour. John’s experience allows him to be one of our best instructors; showing first time sailors the ropes and teaching experienced sailors new tricks. John is also instrumental in commissioning new Hunter, Elan, Impression and Dufour Yachts through our sister company, Performance Cruising Yachts.

Our skippers:

We are very proud of our skippers, who are all first-rate sailors, warm and friendly and have a good knowledge of the many attractions and interesting sites around the harbour. We receive many, many compliments about our skippers, who can turn a great day's sailing into an outstanding day. They are chosen for their great personalities, experience and qualifications. Many of our skippers have been with Sydney By Sail for many years. We have the friendliest team in the sailing business.