Business Details
31 Years
experience
Experience Sydney Harbour with Premium Sailing Adventures
Established in 1995, Sydney By Sail has spent three decades redefining sailing experiences on Australia's most iconic waterway. Our journey began with a vision to make sailing accessible to all, and today we operate Sydney's newest fleet of luxury yachts ranging from 31 to 50 feet. Through our internationally accredited sailing school, we've trained thousands of sailors while pioneering innovative programs like our Mile Builders expeditions along Australia's east coast. Our team comprises Olympic athletes, world championship competitors, and certified instructors who bring unparalleled maritime expertise to every experience.We've become Sydney's premier sailing provider by combining cutting-edge vessels with personalized service, creating unforgettable moments for everyone from first-time sailors to seasoned professionals. Our commitment to excellence has earned us prestigious awards including NSW Enterprise Awards and Telstra Small Business Award nominations, while maintaining our position as Australia's exclusive dealer for renowned yacht brands like Elan and Dufour.
Services
Daily Sailing Trips
Private Yacht Charter
Sailing School Courses
Corporate Team Building
Romantic Getaways
Details
- Year established: 1995
Highlights and features
- 30+ years pioneering sailing experiences on Sydney Harbour
- Internationally accredited training programs with IYT certification
- Newest luxury yacht fleet in Australia (31-50ft vessels)
- Olympic athletes and world championship instructors
- Customized corporate team-building regattas for groups 14-400
Associations and certifications
- IYT Worldwide
What people say
Incredible experience
Professional staff
Unforgettable adventure
Expert guidance
World-class team
Services
Sailing School
Our IYT-accredited sailing courses transform beginners into confident sailors through hands-on training on Sydney Harbour. With expert instructors including Olympic athletes and world championship competitors, we offer programs from basic yachting skills to international certification. The 2-day Introduction to Yachting course provides fundamental skills while advanced packages prepare sailors for global adventures, all using our modern fleet of Hunter, Elan, and Dufour yachts.
Private Charter
Experience Sydney Harbour aboard luxury yachts ranging from 31 to 50 feet with professional skipper service. Our private charters accommodate groups from intimate couples to 25-person celebrations, featuring gourmet catering options and customizable itineraries. From sunset cruises to multi-day adventures, our fleet includes state-of-the-art vessels like the Elan E6 performance yacht and Cervetti 44 catamaran for unforgettable maritime experiences.
Team Building
Transform workplace dynamics through competitive sailing regattas on Sydney Harbour. Our corporate programs accommodate groups from 14 to 400 participants across multiple formats including Bronze Regattas for team bonding and Treasure Hunts combining navigation challenges with maritime adventure. Professional skippers guide teams through collaborative sailing tasks that enhance communication and leadership skills in a dynamic outdoor environment.
Romantic Getaways
Indulge in overnight luxury yacht experiences featuring gourmet catering and premium accommodations. Our tiered packages (Gold, Platinum, Diamond) offer 16-24 hours of exclusive vessel access with sightseeing tours followed by unaccompanied stays. Guests enjoy personalized itineraries including harbor landmarks, secluded bays, and sunset cruising, with modern amenities across mid-range to flagship vessels in our fleet.
Mile Builders
Build practical sailing experience through coastal voyages from Sydney to Mackay and Hamilton Island Race Week participation. These guided expeditions on high-performance yachts like the Elan E6 develop advanced navigation and boat handling skills under expert supervision. Designed for certification preparation or skill enhancement, journeys include whale watching opportunities and diverse sailing conditions along Australia's east coast.
People
Matt Hayes
Founder & Managing Director
Olympic sailor and founder of Sydney By Sail, Matt has over 30 years' experience including Sydney to Hobart races and global circumnavigation. He established the business after winning the 1994 NSW Enterprise Workshop Award for Best Business Plan.
Aaron Chadwick
Sailing School Principal
With 20 years' sailing experience including British international competition and Mediterranean yachting, Aaron holds Yachtmaster Offshore certification. He brings competitive racing expertise and a passion for teaching sailing fundamentals to his role as principal instructor.
Josh Hayes
Chief Operating Officer
Qualified Yacht Master Offshore with extensive ocean passage experience, Josh combines maritime expertise with business management skills. He oversees operations while maintaining hands-on involvement in customer experiences on Sydney Harbour.
Rhys Cameron
Fleet Manager
Canadian competitive sailor turned Yachtmaster Instructor, Rhys brings international racing experience and Indian Ocean passage expertise. He manages our diverse fleet while sharing his passion for Sydney Harbour's unique sailing conditions.
Questions
What sailing experiences are available for first-time sailors?
Our Daily Sailing Trips and Try Sailing Experience provide perfect introductions with professional skippers guiding guests through hands-on sailing activities on Sydney Harbour.
Can we customize corporate team-building events?
Yes, we offer multiple formats including Bronze/Silver Regattas, Treasure Hunts, and Point-to-Point races with customizable durations from 2 to 8 hours for groups 14-400.
What certifications do your instructors hold?
Our instructors hold IYT Worldwide certifications up to Yachtmaster Offshore level, with many having competed in Sydney to Hobart races and international competitions.
Are overnight yacht charters available?
Yes, our Romantic B & B Packages offer 16-24 hour luxury yacht charters with gourmet catering, including Gold, Platinum, and Diamond tier options with varying durations and amenities.
How do sailing lessons work for beginners?
The 2-day Introduction to Yachting course teaches fundamental skills with small class sizes, progressing to advanced certifications through our International Crew and Skipper Packages.
What's included in private yacht charters?
Private charters include professional skipper, gourmet catering options, premium vessels from 31-50ft, and customizable itineraries featuring Sydney Harbour landmarks and secluded bays.
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