ESTABLISHED ON SYDNEY HARBOUR SINCE 1995

EXPERIENCE SYDNEY HARBOUR WITH SYDNEY BY SAIL

From unforgettable harbour experiences and corporate events to expert training and yacht ownership, your journey starts here.
4.9/5 stars on Google Reviews

Innovation, Legacy, and Australia’s Premier Sailing Fleet.

Established in 1995, Sydney By Sail is one of Sydney Harbour’s largest and most respected yacht charter and sailing companies.

Based in Sydney, we operate one of the newest fleets of performance and luxury yachts on Sydney Harbour.

For more than 30 years, our clients have trusted our experienced team to provide safe, professional and memorable sailing experiences, from private leisure and corporate events to sailing training and yacht ownership opportunities.
Why Choose Sydney By Sail

More Than a Yacht Charter Company

Sydney By Sail is part of a substantial Australian marine business whose activities, services and products extend across the sailing and recreational marine industry.

Through our sister company, Performance Cruising Yachts, the broader business represents an extensive portfolio of leading international yacht, catamaran and powerboat brands in Australia, including:

International Brands We Represent

Sailing Trips, Private Yacht Charter, Corporate Events & Sailing School in Sydney

Explore Sydney Harbour your way, from relaxed sailing trips and romantic getaways to private charters, corporate events, sailing courses and yacht share opportunities.

Daily Sailing Trips

Join our shared 3 HR hands-on or sightseeing sailing experience. Take the helm or sit back and relax as the skipper guides you about the Harbour under sail.

Private Charter

Privately Chartering a Yacht is the perfect way to experience Sydney Harbour with a group of friends or family. Our Luxury Fleet ranges from 31ft – 45ft and can be chartered 24/7...

Sailing School

Become confident, competent and certified with our internationally accredited Sailing School through IYT. Courses from beginner through to International Bareboat Skipper...

Team Building

Arrange a unique and exciting Team Building Event sailing luxury yachts on Sydney Harbour. No previous experience necessary,

Romantic Getaways

Enjoy our unique & popular Romantic B&B Packages – imagine private skipper, gourmet catering, and an evening unaccompanied onboard a luxury yacht.

Yacht Share

Invest in an economic and accessible Yacht Share syndicate allowing 10% owners 33+ days of yachting a year on Sydney Harbour & beyond.
Testimonials

Hear from people who have sailed, trained and celebrated with Sydney By Sail.

Posted on Google Google
Michael martin profile picture
Michael martin
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What a fantastic day! I did the Introduction to Sailing course and couldn't recommend it more highly. The boat was beautiful, the setting is stunning, and our captain Will was amazing, incredibly knowledgeable, patient, and clearly loves what he does. What I appreciated most was how much actual hands-on sailing we did out on the harbour. It wasn't just watching and listening, we were on the ropes and at the helm from early on, and my confidence grew enormously over the day. If you've ever been curious about sailing, this is the perfect way to start. Five stars, and a huge thanks to Will!
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Kim Arnott profile picture
Kim Arnott
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What am amazing day, our skipper was Mike, a young man with a passion of sailing. Greeted with smiles from all staff once on the jetty. Thankyou for a sydney harbour experience that we will talk about and recommend Sydney by Sail for many years to come.
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Charles Van Damme profile picture
Charles Van Damme
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We did the full skipper course with Sydney by Sail and had a great time, especially on the 3 day 2 night live aboard sail from Sydney to Pittwater. Highly recommend Sydney by Sail to get your skipper license!
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Marnix Denys profile picture
Marnix Denys
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We did the bareboat skipper course and VHF course. Both Marc and James were great, knowledgeable skippers. Learned a lot and the 3 day live aboard was amazing. We encountered dolphins, seals and whales. Thanks for the wonderful experience.
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Millie Webb profile picture
Millie Webb
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Kevin Shixiao He profile picture
Kevin Shixiao He
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Amazing sail with capitain Ollie. He was friendly and professional! Shoutout to Josh who made our last minute trip possible! Great experience!
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Donald Watt profile picture
Donald Watt
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As someone visiting Sydney for the first time, this was the perfect way to see the city. Captain Olly was both friendly and very knowledgeable of the area. A truly memorable experience. Highly recommend 👍
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tim neale profile picture
tim neale
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Great people to deal with always make you feel welcome
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Jacquelyn Cox profile picture
Jacquelyn Cox
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Edit: We have amended our review to reflect the efforts of Josh & the Sail By Sydney team to rectify our experience. As we could not take them up on the offer of a re-sail, (we live across the world & this was a once in a lifetime trip) Josh & the team donated the experience to Beyond Blue in our name. This was a very positive way to rectify our experience and we truly appreciate their willingness to ensure we felt valued. Thank you Josh & Team. Original Review: We booked the Daily Sailing Trip from 1pm–4pm in November expecting a unique harbor sail. We understand that this booking was on a sailboat and not marketed as a "tourism, informational" harbor sail. Our expectations were pretty simple: a nice sail around the harbor with occasional commentary on where we are going. Online it says we will sail past the Sydney Harbour Bridge, Opera House, Fort Denison, Clarke & Shark Island. I am certain we didn't hit the last 2 sites but we might have - our Captain never mentioned any of the sites to us. Overall, the experience was fine, but several aspects didn’t align with how this tour is marketed: First and foremost, we docked back at 3:30pm instead of the scheduled 4pm. We also departed late while we waited for a couple who was running late. I believe we left at around 1:20pm. Additionally, our Daily Sail was combined with a Crew Sail without warning. While this is understandable operationally, the boat ended up feeling extremely overcrowded. On top of that, the day was very windy, which meant none of the passengers could explore the boat so we all had to sit on top of each other. With a full boat & the Crew Sail passengers learning to sail, we were squished together, stepping around each other on pretty rocky waters. This setup likely would have been totally fine if we had signed up for a Crew Sail, but we didn’t. I wish we were given the opportunity to reschedule so we were not on squished on what was actually a Crew Sail. The captain was clearly a capable instructor for the two people learning to sail, but for the rest of us, there was very little narration or information about where we were sailing or what we were seeing along the harbor. I did enjoy the chance to steer the boat but that would have been part of the Daily Sail regardless. Most of the information we overhead from the Captain speaking to the 2 crew passengers was about where he sailed previously, his sail club locations, and some info on the boats around us. Ultimately, for $510 marketed as a Daily Harbor Sail, the experience was a pretty big letdown. Not a bad time overall, but it didn’t deliver what was advertised, especially for those not wanting a full sailing lesson focused around 2 passengers rather than the 8 other passengers who signed up for the Daily Sail. I was able to capture some nice photos but not worth the $510. I could have gotten the same photos from the Manly Ferry for a few bucks.
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Oskar Milton profile picture
Oskar Milton
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Great bunch of lads, had pleasure of dealing with Josh. An amazing way to see the sites of our beautiful harbour!!

Chart Your Course with Sydney By Sail

Sydney By Sail offers much more than yacht charter. From unforgettable sailing experiences and professional training to yacht ownership and management, we provide a broad range of opportunities on Sydney Harbour.

Explore our services below or get in touch to find the right experience for you.
Sailing Experiences & Charters
Private yacht charters, romantic overnight stays and memorable sailing experiences on Sydney Harbour.
Corporate Sailing & Events
Corporate functions, team-building activities, client entertainment and group experiences.
Sailing Training & Mile Building
Practical sailing courses and mile-building opportunities for different experience levels.
Yacht Ownership & Management
Yacht ownership, syndication and shareholder opportunities, supported by professional yacht management.
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Established in 1995, Sydney By Sail is one of Sydney Harbour’s largest and most respected yacht charter and sailing companies, offering experiences, training, corporate events and pathways to yacht ownership.