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 - 2028 Trip calendar
Trans-Tasman Sydney to Auckland Race
7 - 22 Oct 2025 | 15 Nights | 1,270nm
Price: from AUD$15,750 - Use code: RACE20 to save $2,000
Book from $7,875 deposit / Balance due after 7/9/25
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
For just the second 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.
Cabbage Tree Island Race | Sydney, Australia
2 - 7 Dec 2025 | 5 Nights | 180nm
Price: from AUD$2,450
Book from $1,225 deposit / Balance due after 7/9/25
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.
Click here for availability or to book
Rolex Sydney Hobart Race | Australia
25 - 31 Dec 2025 | 8 Nights | 630nm
Price: from AUD$13,750 - Crew Full, Join Waitlist
Book from $3,550 deposit / Balance in 2 payments after 26/9/25
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 - Crew Full, 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 calendar
Trans-Tasman Sydney to Auckland Race
24 Feb - 11 Mar 2026 | 15 Nights | 1,270nm
Price: from AUD$11,750
Book from $3,930 deposit / Balance in 3 payments after 26/11/25
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 - 29 Mar 2026 | 21 Nights | 820 nm
Price: from AUD$9,750
Book from $2,490 deposit / Balance in 3 payments after 8/12/25
Yacht: Silver Fern
Two Yacht Sailing Expedition
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 - 29 Mar 2026 | 21 Nights | 820 nm
Price: from AUD$9,750
Book from $2,490 deposit / Balance in 3 payments after 8/12/25
Yacht: Te Kaihōpara
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 competitors an exhilarating 384-nautical-mile journey along the stunning New South Wales and Queensland coastlines.
Rolex Sydney Hobart Yacht Race | Australia
25 - 31 Dec 2026 | 6 Nights | 630nm
Price: from AUD$17,750 - Crew Full, Join Waitlist
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 calendar
Sydney to Noumea Yacht Race
25 May - 4 Jun 2027 | 10 Nights | 1,064nm
Price: from AUD$7,750
Book from $1,960 deposit / Balance in 3 payments after 24/11/26
Yacht: Awen
Ocean Race
Options: 9 Single Berths / Shared Cabins
Join the crew for an epic blue water classic from Sydney to Nouméa, New Caledonia. This premier 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 81st edition of the race has a fleet in excess of 100 yachts expected.
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 81st edition of the race has a fleet in excess of 100 yachts expected.
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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