DARLING HARBOUR, SYDNEY  -  Phone: +61 2 9280 1110 - [email protected]

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.

Matt Hayes

Managing Director and Founder

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.
Matt is now managing Sydney By Sail and its sister company Performance Cruising Yachts, exclusive importer of the Slovenian Elan Yachts.

Matt has recently completed a life goal of his, circumnavigating the world on SV Influencer over 2 years from 2018 – 2020. 

Ed Penn

General Manager

Ed started in January 1997 and has over 30 years of experience within the marine industry and brings a massive wealth of knowledge and expertise to all areas of the business.

Ed is passionate about sailing and runs Sydney By Sail. Growing up on the East Coast of England, he was sailing competitively from an early age. He then studied Science (Bachelor Hons) at Sheffield University. Eager to improve his sailing skills , he then became a sailing instructor and a commercial skipper. Ed spent also quite some time in shipyards in various locations: the USA, Slovenia, Croatia, France and has developed a strong network in the sailing industry.

Ed is a key member of our team and thanks to his dedication Sydney By Sail won several awards in Customer Service.

Josh Hayes


Josh has grown up with Sydney By Sail. His interests range from surfing, surf-life saving, windsurfing & sailing.

Josh is devoted to making your sailing experience one to remember. He takes pride in sharing Sydney Harbour with people from all around the world. 

Josh has a double degree of Commerce and Psychology majoring in Marketing at Macquarie University, as well as a Yacht Master Offshore certificate. 

Josh has done several notable ocean passages, including: Reunion Island to Capetown, Recife (Brazil) to Grenada (Caribbean) & more locally Hobart – Lord Howe Island – Sydney. Having been lucky enough to travel the world by water, Josh still considers Sydney harbour to be the best waterway in the world. 

Josh’s role at Sydney By Sail varies greatly, from answering the phones and arranging bookings, to Social media marketing, to toilet cleaner – whatever needs doing – Josh will be there!

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.

Our Skippers are chosen for their great personalities, experience and qualifications. Many  have been with Sydney By Sail for many years. We have the friendliest team in the sailing business.


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Festival Pontoon
National Maritime Museum
2 Murray Street,
Darling Harbour NSW 2000
Telephone: +61 2 9280 1110
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