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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 has over 20 years experience within the marine industry and has a massive wealth of knowledge and expertise to all areas of the business.  He supervises the entire operation, on a day to day level and strategic planning and development.  Ed is passionate about sailing and the yachts that we use for charter and private sales and it shows.  Growing up on the east coast of England, he was sailing competitively from early age and continued to do so whilst studying at Sheffield Hallam University where he graduated with a Bachelor of Science Degree, he also became a sailing instructor and commercial skipper to allow him to pass on his skills and love for the sport.  To further his understanding of the yachts we use and sell he has spent time at the various shipyards in the USA, Slovenia, Croatia and France and has developed strong relationships with the key personnel in both sales and the after sales departments.  Due to Ed’s dedication to service, our company has been awarded numerous Awards for Customer

Neil Easson – Operations and Fleet Manager

Neil is a highly qualified and season mariner that developed his seamanship skills whilst working in the Caribbean aboard luxury super yachts engaging in deliveries and Atlantic crossings on vessels up to 130ft. Retained as 1stMate he toured the world until finally returning to Australia in 2002 where he continued his studies to gain a Certificate IV in Marine Operations (Formally known as Master Class 4) and is able to master vessels up to 35m commercially. Neil also has extensive experience working on large motor cruisers, specifically the Sunseeker brand where he for many years was master aboard a 34m model and later a 38m model for which he oversaw the build in the UK, on behalf of the owner, its commissioning and launch. Neil also has a commercially endorsed Yacht Master Ocean certificate and is a valued member of our team responsible for a range of commissioning duties, deliveries, private tuition and after sales services.

Clive Shute - Senior Skipper & Instructor

Clive is our resident Round-The-World-Sailor with a particular penchant for cooler climates, with voyages throughout the Arctic and Antarctica regions. On his last three year voyage he circumnavigated North and South America, including the South Pacific Islands and the Caribbean on a 112ft sailing yacht. Clive also possesses an impressive list of marine qualifications, both commercial and recreational. His solid engineering skills, excellent communication and meticulous approach to maintenance make him an asset to the team.

Alan Dickenson - Offshore Senior Instructor and Skipper

There is little that Alan does not know when it comes to teaching sailing..  He is responsible for the offshore sailing courses we offer and is the cheif examiner for the International Certificate of Competency Assessment.  With an engineering background, Alan has a mind for facts and figures and has the ability to explain the most complex of navigational tasks with ease.  He is well liked amongst his students and fellow skippers and is a true assest to the team.

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.