Darling Harbour – Sydney – Australia
About Us
Our Story

Sydney By Sail was established in 1995 and now celebrating 25 years in business.

We specialise in Yacht Share, Yacht Charter, Ownership Programmes, Sail Training, Corporate Team Building and Unique Overnight Packages.  We only use new premium boat brands with links to the manufacturer this is through our sister company Performance Cruising Yachts that has been an importer of luxury yacht and power boat brands since 2003.  This enables us to keep our fleet in excellent condition due to good access to spare parts, warranty replacement and technical support.  Our base has a full service facility for repairs and maintenance .  In short we are a one-stop-shop for all things sailing. 

Award Winning: Sydney By Sail has won many achievements including  the NSW Enterprise Award, The City of Sydney Award for business excellence and twice been nominated as a finalist in the Telstra Small Business Awards.

Matt Hayes


Sailing has been Matt’s passion since he was a boy, taking to the waters of Sydney Harbour with his father and uncle. Matt went on to win many state and national championships, and represented Australia in many world championships with many podium finishes, as well as Admirals Cups and Kenwood Cups. The pinnacle of his competitive career was in 1996, when Matt represented Australia in the Soling Class at the Atlanta Olympic Games, held in Savannah, Georgia. Matt has competed in many Sydney to Hobart Yacht Races – the first at just 18 years of age as helmsman on board Police Car – and 10 as principle helmsman of Ragamuffin IOR, IRC and TP 52 again with many podium finishes.
From Manly Juniors to Cherubs, to 16 foot skiffs and 100 ft super maxis, Matt is renowned for his helming ability and his ability to read the waves and the wind. He also knows how to teach other people to sail, starting his first sailing school at 17 years of age.
His passion is to share his love of wind and ocean – to introduce new people to the joys of sailing. He wishes to pass on his knowledge to maximise performance and enjoyment during the customer experience.

Edward Penn

General Manager

Ed has over 20 years experience within the marine industry and brings a massive wealth of knowledge and expertise to all areas of the business. He supervises the entire purchase process from the initial enquiry, build specification, shipping, commissioning to hand over and after sales. He has a hawk eye for detail when it comes to fit, finish and final delivery to the customer. Ed is passionate about sailing and the yachts that we sell 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 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 Service

Sydney by Sail Team

Our experienced team is on site 7 days a week.

They can assist you with departure and return docking. 

All of our staff are commercial qualified as skippers.

When a Share Owner, you can engage them for:

  • extra training, where required
  • to take the helm whilst you relax and entertain your family and friends.
  • tips and advice on best anchorages
  • induction refresher with on board systems

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