Book your new south wales sailing Adventure
Set sail aboard one of our three exceptional yachts and discover the breathtaking coastline and offshore wonders of New South Wales. From remote expeditions to Middleton Reef, Elizabeth Reef, Balls Pyramid, and Lord Howe Island, to iconic events like the Rolex Sydney Hobart Yacht Race, or scenic coastal passages from the Gold Coast to Sydney, there’s a sailing adventure to match every passion. View all upcoming events in the Sailing Calendar. Manual trip booking form and custom payment plan options available here. View Trip Reviews.
Starting from $464pp per day all inclusive
2025 - 2027 New South Wales calendar
Cabbage Tree Island Race | Sydney, Australia
2 - 7 Dec 2025 | 5 Nights | 180nm
Price: from AUD$1,950
Yacht: Awen
Coastal Race
Options: 9 Single Berths / Shared Cabins
The Cabbage Tree Island Race is a key offshore challenge on the Cruising Yacht Club of Australia calendar, offering 172nm of tactical sailing along New South Wales’ coast. This is a crew qualifying passage for the Rolex Sydney Hobart Yacht Race.
Rolex Sydney Hobart Race | Australia
25 - 31 Dec 2025 | 8 Nights | 630nm
Price: from AUD$13,750 - Last crew position available
Full payment required
Yacht: Silver Fern
Ocean Race
Options: Max 12 Single Berths, Shared Cabins
The Rolex Sydney Hobart Race is one of the toughest and most respected ocean races in the world. It’s the only major race that starts in a harbour, takes in a passage and finishes in a river. This will edition of the Rolex Sydney Hobart Race, with a fleet in excess of 100 yachts expected.
Rolex Sydney Hobart Race | Australia
25 - 31 Dec 2025 | 6 Nights | 630nm
Price: from AUD$17,750 - SOLD OUT - JOIN WAITLIST
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
The Rolex Sydney Hobart Race is one of the toughest and most respected ocean races in the world. It’s the only major race that starts in a harbour, takes in a passage and finishes in a river. This will be the 80th edition of the Rolex Sydney Hobart Race, with a fleet in excess of 100 yachts expected.
2026 New South Wales calendar
Trans-Tasman Sydney to Auckland Race
24 Feb - 11 Mar 2026 | 15 Nights | 1,270nm
Price: from AUD$13,750
Book from $4,950 deposit / Balance on 2/1/26
Yacht: Awen
Ocean Race
Options: 10 Single Berths / Shared Cabins
For just the third time in decades we will see a fully crewed Category 1 yacht race from Australia to New Zealand. The race will start on Sydney Harbour and finish in the Auckland Harbour.
Sydney to Lord Howe Is. to Southport Australian Expedition
8 - 22 Mar 2026 | 14 Nights | 820 nm
Price: from AUD$5,750
Book from $1,700 deposit / Balance in 2 payments after 7/1/26
Yacht: Silver Fern
Two Yacht Sailing Expedition / Sailing days 8 / Exploring days 6
Options: Max 8 Single Berths, Shared Cabins
Sail from Sydney, exploring the eastern coastline of NSW, offshore to Balls Pyramid, Lord Howe Island, Elizabeth and Middleton Reef’s and the golden shores of Southport. Hoist the sails for a unique journey.
Sydney to Lord Howe Is. to Southport Australian Expedition
8 - 22 Mar 2026 | 14 Nights | 820 nm
Price: from AUD$4,950
Book from $1,500 deposit / Balance in 2 payments after 7/1/26
Yacht: Te Kaihōpara / Sailing days 8 / Exploring days 6
Two Yacht Sailing Expedition
Options: Single/Double Berths | Private Cabin | Maximum Guests: 10
Sail from Sydney, exploring the eastern coastline of NSW, offshore to Balls Pyramid, Lord Howe Island, Elizabeth and Middleton Reef’s and the golden shores of Southport. Hoist the sails for a unique journey.
Sydney to Gold Coast Yacht Race | Australia
22 - 29 Jul 2026 | 7 Nights | 384nm
Price: from AUD$5,250
Book from $1,320 deposit / Balance in 3 payments after 23/1/26
Yacht: Awen
Coastal Yacht Race
Options: Single Berth | Maximum berths: 9
The Sydney to Gold Coast Yacht Race is one of Australia’s premier offshore sailing events, offering a thrilling 384-nautical-mile challenge along the stunning east coast. In the next edition of the race, sailors will once again test their skills, endurance, and strategy as they navigate changing weather conditions and tactical obstacles on the journey north.
Rolex Sydney Hobart Yacht Race | Australia
25 - 31 Dec 2026 | 6 Nights | 630nm
Price: from AUD$17,750 - SOLD OUT - JOIN WAITLIST
Book from $4,445 deposit / Balance in 3 payments after 26/6/26
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
This race is one of the toughest and most respected ocean races in the world. It’s the only race that starts in a harbour, takes in a passage and finishes in a river. This will be the 80th edition of the Rolex Sydney Hobart Race, with a fleet in excess of 100 yachts expected.
2027 New South Wales calendar
Sydney to Noumea Yacht Race
25 May - 4 Jun 2027 | 10 Nights | 1,064nm
Price: from AUD$6,750
Book from $1,980 deposit / Balance in 3 payments after 24/11/26
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
Set sail on an epic 1,064-nautical-mile blue water classic from Sydney to Nouméa, New Caledonia. This premier ocean race is a true test of endurance, strategy, and seamanship, taking crews from the rugged coastline of Australia across the Tasman and Coral Seas to the tropical paradise of Nouméa.
Rolex Sydney Hobart Yacht Race | Australia
25 - 31 Dec 2027 | 8 Nights | 630nm
Price: from AUD$13,750
Book from $3,460 deposit / Balance in 3 payments after 26/6/27
Yacht: Silver Fern
Ocean Race
Options: Max 12 Single Berths, Shared Cabins
The Rolex Sydney Hobart Race is one of the toughest and most respected ocean races in the world. It’s the only major race that starts in a harbour, takes in a passage and finishes in a river. This edition of the Rolex Sydney Hobart Race, has a fleet in excess of 100 yachts expected, ranging from 36 to 100 foot in length. The electric pre-race village atmosphere at the Cruising Yacht Club of Australia (CYCA) followed by the excitement of the build-up to the start on Sydney Harbour on Boxing Day is hard to describe.
Rolex Sydney Hobart Yacht Race | Australia
25 - 31 Dec 2027 | 6 Nights | 630nm
Price: from AUD$17,750
Book from $4,430 deposit / Balance in 3 payments after 26/6/27
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
The Rolex Sydney Hobart Race is one of the toughest and most respected ocean races in the world. It’s the only major race that starts in a harbour, takes in a passage and finishes in a river. This edition of the Rolex Sydney Hobart Race, has a fleet in excess of 100 yachts expected, ranging from 36 to 100 foot in length. The electric pre-race village atmosphere at the Cruising Yacht Club of Australia (CYCA) followed by the excitement of the build-up to the start on Sydney Harbour on Boxing Day is hard to describe.
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Categories: All Events | Coastal Passages | Cruises | Expeditions | Ocean Passages | Racing
Destinations: Australia | Fiji | New Zealand | Vanuatu | South Pacific | NSW | QLD | NT | TAS | WA
Yachts: Awen | Sea Breeze III | Silver Fern | Te Kaihōpara