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.Â
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
Adrian Carter
Trustindex verifies that the original source of the review is Google.
Josh & the team have a fantastic selection of yachts & catamarans to suit all occasions. Their wealth of knowledge and expertise is second to none. Every time we head out with them is a fantastic new experience.
Can’t recommend highly enough! 5 star
Posted on Google
Mrs P
Trustindex verifies that the original source of the review is Google.
How to beat the January blues? Get out on the water! We left the snow and ice in the UK to visit family in Sydney and really wanted to explore the beautiful harbour. We heard the best way to see it is from the water and felt like luxuriating on ‘our own’ yacht for an afternoon so off we trotted to Sydney By Sail in Darling Harbour.
The whole set up is really friendly and professional. From easy booking with the office crew, who accommodated all our party’s needs, to getting on board with our knowledgeable and experienced skipper Ollie, we had the best time. We were asked what we wanted to see and do so had a sail around some of the iconic landmarks, sailing under the harbour bridge and past the opera house, under full sail, is breathtaking. Skipper Ollie was a lot of fun and a great tour guide, we learned loads about the different parts of the harbour. Those of us who wanted to could have a go on the helm and help with tacking, and we felt in safe hands the whole time.
We wanted to moor up for a lunch stop and a swim and Ollie knew the best little bays to park in. The boats are spacious and well equipped for rustling up your BYO feast. Didn’t want to leave!
We’ll definitely be back next time we visit family. Thanks Sydney by Sail’s Josh and Ollie - hands down the best experience we’ve had this trip!
Posted on Google
Keith
Trustindex verifies that the original source of the review is Google.
We booked a 3 hour sail on the harbour. Captain James was great, explaining the sights of Sydney as well as some basic seamanship for us desert dwellers. Fantastic experience.
Posted on Google
ajp112233
Trustindex verifies that the original source of the review is Google.
Great day sailing with this company. Love the welcoming and easy going nature from Josh through to all his team. Hugely experienced team (they had there recently complete Sydney Hobart boat on the dock) and they make it an unforgettable experience. Sailing under the Harbour Bridge and past the Opera House can need get old. Thankyou everyone at SBS.
Posted on Google
Jacquelyn Cox
Trustindex verifies that the original source of the review is Google.
Edit: Hi Josh, we emailed you via your website contact page but have not heard back from you or the company. Thank you!
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
Cameron Jeffries
Trustindex verifies that the original source of the review is Google.
As someone who lives in Sydney, the daily sail was such a good way to see my city in a different way and a perfect way to spend the afternoon. Passing by some iconic sites whilst getting involved with sailing the ship was really fun.
Our Skipper, James, was great; very informative and accomodating.
I’ve seen that Sydney By Sail offer lots of other experiences which also look great. In particular, I’m keen to join their intro to sailing course soon.
Posted on Google
Simon Moore
Trustindex verifies that the original source of the review is Google.
We did the Daily Sail on a beautiful summer day.
When we arrived, we were greeted by the very friendly Ollie in the reception where the crisp air conditioning was very welcome. We were offered sodas for our sail ahead, which was a nice touch.
For our tour, we had Captain James (Sparrow?). We were on Tumbalong - a lovely 41-foot sailing yacht. We cruised through the harbour, past the iconic Sydney landmarks, until we reached the heads.
Captain James was a great host and helmsman. He drew our attention to all of the best spots within our vantage.
All of us on the boat (4x) were able to steer the ship as much or as little as we liked. Captain James explained the fundamentals of sailing, and we could get involved in trimming the sails.
The Sydney harbour sail made for excellent selfies and photos. We of course had to bust out the captain’s hat!
Captain James left us in full control of the experience. We elected to sail at a fairly leisurely pace, taking the time to soak in the beautiful views, compared to the ferries which would be racing past. We could get quite close to the shorelines before tacking and continuing on our way.
The boat itself was clean, well-equipped, and kept our BYO beers cold all afternoon. The galley had facilities for us to prepare some food we had brought with us.
We set sail at 1pm sharp and docked back just on 4pm.
All in all, this was a great experience. I would recommend this for many kinds of occasion. On our daily sail was a recently married couple, but I can see how this would make for a great work team event or frankly even showing up solo if you want to get some time behind the helm.
Bravo!
Posted on Google
Carla Woolley
Trustindex verifies that the original source of the review is Google.
Enjoyed an overnight charter with Sydney by Sail! Captain James was fantastic and took us for a sail around Sydney Harbour. The boat was perfect and had everything we needed. We were very lucky with the weather and enjoyed a beautiful sunrise.
Highly highly recommend as an activity with your partner or a group of friends!
Posted on Google
MC
Trustindex verifies that the original source of the review is Google.
We had a lovely stay with Sydney by Sail (B&B experience). The afternoon sail around the harbour was absolutely beautiful. The boat was surprisingly spacious and felt like our own little private retreat on the harbour for the evening. Waking up on the water was absolutely unforgettable. A truly unique and relaxing B&B experience. We'll definitely be back!
Posted on Google
Enya Berg
Trustindex verifies that the original source of the review is Google.
Ein super Erlebniss! Ich verbrachte 3 wunderschöne Studen auf dem Segelbot im Hafen von Sydney. Ich fühlte mich die ganze Zeit sicher und hatte sogar die Gelegenheit selber mitanzupacken und das Boot zu steuern :).
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.