Innovation, Legacy, and Australia’s Premier Sailing Fleet.
Sydney by Sail is a dynamic leader in the Australian maritime industry, offering three decades of expertise in luxury yacht charters.
Our commitment to innovation is reflected in our fleet—the newest in the country—which features a curated selection of performance and luxury yachts.
Whether hosting an elite corporate event or a private leisure excursion, our clients benefit from a 30-year track record of safety, professionalism, and unrivaled harbour expertise.
Why Choose Sydney By Sail
Sydney By Sail has the newest fleet of yachts in Sydney Harbour.
Our sister company, Performance Cruising Yachts, exclusively imports world-class yacht brands to Australia, including Hanse Yachts, offering flexible ownership options - shared, outright, or charter.
Sailing Trips, Private Yacht Charter, Corporate Events & Sailing School in Sydney
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.
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...
Become confident, competent and certified with our internationally accredited Sailing School through IYT. Courses from beginner through to International Bareboat Skipper...
And we are very proud of the amazing testimonials past and present clients have graced us with….
Posted on Google
Michael martin
Trustindex verifies that the original source of the review is Google.
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!
Posted on Google
Kim Arnott
Trustindex verifies that the original source of the review is Google.
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.
Posted on Google
Charles Van Damme
Trustindex verifies that the original source of the review is Google.
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!
Posted on Google
Marnix Denys
Trustindex verifies that the original source of the review is Google.
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.
Posted on Google
Millie Webb
Trustindex verifies that the original source of the review is Google.
Posted on Google
Kevin Shixiao He
Trustindex verifies that the original source of the review is Google.
Amazing sail with capitain Ollie. He was friendly and professional! Shoutout to Josh who made our last minute trip possible! Great experience!
Posted on Google
Donald Watt
Trustindex verifies that the original source of the review is Google.
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 👍
Posted on Google
tim neale
Trustindex verifies that the original source of the review is Google.
Great people to deal with always make you feel welcome
Posted on Google
Jacquelyn Cox
Trustindex verifies that the original source of the review is Google.
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.
Posted on Google
Oskar Milton
Trustindex verifies that the original source of the review is Google.
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’s Premier Sailing Specialists.
Ready to experience Sydney Harbour from the deck of Australia’s newest luxury fleet?
Whether you are planning an elite corporate event, a private leisure escape, or a world-class tourism experience, our team is here to tailor the perfect itinerary.
Reach out today to discuss your requirements and let us welcome you aboard our performance yachts.
Corporate Events
Inquire about team building, networking, and executive hosting.
Private Leisure
Book a luxury day out or a sunset sail for friends and family.
Tourism Inquiries
Partner with us for high-end travel itineraries and group tours.
The Fleet
Ask about specific performance specifications or luxury amenities.
Sydney by Sail is a dynamic leader in the Australian maritime industry, offering three decades of expertise in luxury yacht charters. Our commitment to innovation is reflected in our fleet—the newest in the country—which features a curated selection of performance and luxury yachts.