• Romance Bed & Breakfast
  • Daily Sailing Trips
  • Private Charter
  • Sailing Videos
  • Team Building
  • Sail, Dine & Stay
  • Sailing School

Welcome to Sydney By Sail

Sydney by Sail is your home on Sydney Harbour for all things sailing.

We offer a range of sailing experiences – including corporate sailing, yacht charter, learn to sail courses, coastal sailing trips, amazing treasure hunts and leisure activities ranging from three-hour sails to luxury overnight stays.

See our yachts under sail on YouTube.  Click Here.

Our fleet of Hunter Yachts boasts the newest yachts in Sydney, with comfortable cabins, roomy cockpits and the latest technology and equipment.

Sydney by Sail is owned and operated by Matt Hayes, who represented Australia at the Atlanta Olympics,has sailed in many Sydney-Hobart yacht races, run several sailing schools and chartered yachts around the world, so he knows his stuff. 

So trim the sheets, take the helm and book now!

Daily Sailing Trips

Explore Sydney Harbour on our three-hour sailing experience - the best way to see the harbour. Get a taste for sailing and see the sights all in one go. Read more...

Private Charter

The best way to explore Sydney Harbour is to charter a yacht for a full or half day. Choose either a Skippered or Bareboat Charter.. Read more...

Romance B&B

When it comes to romantic evenings, this is as good as it gets ... lazing on a luxury yacht, enjoying delicious cuisine on Sydney Harbour. Read more...

Team Building

For those organising a team building event for staff or a unique way to to entertain or impress clients upon our harbour. Read more...

Twilight Sail

Let the fresh sea breeze blow out the cobwebs of your week, sail under the Sydney Harbour Bridge, past the Sydney Opera House. Read more...

Sail School

Sydney By Sail is fully accredited with International Yacht Training Worldwide & exclusive provider of IYT courses on Sydney Harbour.  Read more...