DARLING HARBOUR, SYDNEY - Phone: +61 2 9280 1110 - [email protected]Turn colleagues into crew with an exciting and accessible yacht-racing experience, balanced with time to relax and unwind anchored in a sheltered cove. No sailing experience is required, with professional skippers guiding every team.
4-6 hours | From $260pp | Groups of 14+ | Darling Harbour
The Regatta & Relax combines the excitement of competitive sailing with time to unwind and enjoy Sydney Harbour with your team.
Your group is divided into crews across a fleet of luxury sailing yachts. Following a welcome and safety briefing, each crew learns the fundamentals of steering, sail handling, communication and race tactics under the guidance of our professional skippers.
Teams then compete in a fun regatta around a course designed for the conditions before the yachts come together in a sheltered harbour location. Guests can relax, enjoy catering and beverages, socialise with colleagues and take in the spectacular surroundings.
No previous sailing experience is required. Guests can take the helm, trim the sails, assist with navigation or simply enjoy the experience at a level that suits their confidence and ability.
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!!
$260 per person
A balanced introduction to yacht racing with time to unwind and enjoy Sydney Harbour after the competition.
Includes a safety briefing, yacht allocation, sailing introduction, crew-role allocation and a fun regatta, followed by time in a sheltered harbour location for catering, beverages and socialising.
$275 per person
Our recommended option for a complete Regatta & Relax experience.
Allows time for a thorough briefing, sailing practice and competitive racing, followed by a relaxed harbour session where guests can enjoy catering and beverages while socialising with their team.
Recommended option
$290 per person
An extended experience with additional time for sailing, crew involvement and racing before settling into a sheltered harbour location.
Ideal for larger groups or teams wanting a more substantial event, with greater flexibility to explore Sydney Harbour and enjoy an extended catering and social session after the regatta.
All prices include GST and are shown in Australian dollars. Catering and beverages are available as additional options. A minimum of 14 participants is required for a multi-yacht event.
Your event team welcomes the group, explains the event format and provides a complete safety briefing.
Participants are divided into crews and introduced to their professional skipper and yacht.
Each crew practises steering, trimming sails, working with the wind and communicating effectively onboard.
Teams review the race course, allocate crew roles and develop their tactics before the competition begins.
The yachts compete in a fun and engaging regatta, with the course adjusted to suit the weather, harbour conditions and selected event duration.
After racing, the yachts settle into a sheltered location where guests can relax, enjoy catering and beverages, socialise with colleagues and take in the harbour surroundings.
The event concludes with race results, team photos and any prizes or presentations before returning to Darling Harbour.
The precise course, racing format and relaxation location are adjusted according to the weather, harbour conditions, group size and selected duration.
No. The Regatta & Relax package is designed to be accessible to complete beginners.
Every yacht has an experienced skipper and crew to provide a safety briefing, explain the sailing roles and guide participants throughout the event. Guests can become actively involved in the sailing or participate at a level that suits their confidence and ability.
We recommend the five-hour package for a complete Regatta & Relax experience.
The four hour option provides a balanced combination of sailing, racing and relaxation, while the five-hour package allows more time for crew preparation, racing and socialising. The six-hour option provides the most substantial experience and is particularly suitable for larger groups or teams wanting an extended afternoon on Sydney Harbour.
A minimum of 14 participants is required for a multi-yacht Regatta & Relax event.
Larger groups are divided across multiple yachts. The number and type of yachts required will depend on final attendance and fleet availability.
Smaller groups can contact Sydney By Sail to discuss suitable private sailing and charter options.
The package includes a fun and engaging regatta before the yachts move into the relaxation portion of the event.
The precise racing format and number of races will depend on the selected duration, weather, harbour conditions and the time required for briefing and sailing practice.
After the regatta, the yachts settle into a sheltered harbour location where guests can relax, socialise and enjoy the Sydney Harbour surroundings.
Catering and beverage packages can be arranged for this portion of the event at an additional cost.
No. Catering and beverages are not included in the per-person Regatta & Relax package price.
A range of catering and beverage packages can be added to the event and tailored to the group size, event duration, dietary requirements and preferred style. Vegetarian, non-alcoholic and other dietary options are also available.
Comfortable casual clothing and enclosed, non-marking shoes are recommended.
Guests should also bring sun protection, a warm layer and weather-appropriate outerwear. High heels are not suitable aboard the yachts.
Sydney By Sail monitors the forecast and harbour conditions before every event.
The race course, sheltered relaxation location or event format may be adjusted to suit the conditions. If the event cannot safely proceed, the organiser will be contacted to discuss the available options in accordance with the booking terms.
A 50% deposit based on estimated attendance is required to secure the yachts, skippers and event team.
Final attendance, catering and beverage selections, pickup and drop-off arrangements, and the remaining balance are due 21 days before the event.
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Festival Pontoon
National Maritime Museum
2 Murray Street,
Darling Harbour NSW 2000
Festival Pontoon
National Maritime Museum
2 Murray Street,
Darling Harbour NSW 2000
Telephone: +61 2 9280 1110
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