Find the best sailing tours and captained boat rentals in New South Wales on Pelago. Plan and book online with the best prices and world class support.

The Best Sailing tours and Captained boat rentals in New South Wales | Updated March 2026

New South Wales

2.5 hour, hands on Sailing experience Sailing on Sydney Harbour.

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Experience the thrill of gliding across the clear waters of Sydney Harbour mastering sailing skills and enjoying the stunning skyline all while becoming part of a dynamic crew.

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Drift along Sydney Harbour aboard the classic yacht Southwinds soaking in stunning views of the Opera House and Harbour Bridge while captivating sailing experiences await you.

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Paddle through Sydney's stunning waterways discovering hidden beaches and soaking in the natural beauty surrounding North Harbour. A perfect way to connect with nature and enjoy time together.

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Sailing on Sydney Harbour aboard the luxurious Calypso offers relaxation and stunning views making it an ideal escape for families and friends alike. Enjoy the gentle breeze and breathtaking scenery.

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Be your own captain and enjoy a scenic 2-hour picnic on an eco-friendly electric boat through Sydney's beautiful Akuna Bay.

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Sail across the stunning waters of Sydney Harbour taking in iconic landmarks while learning sailing skills alongside experienced skippers. A perfect blend of adventure and unforgettable views awaits!

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Experience Sydney's stunning waters as you glide effortlessly in a deluxe double sea kayak perfect for leisurely paddles or enjoyable picnics on the water.

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Captain your very own electric picnic boat with no experience or boat license required. Sail the Parramatta River and explore Sydney from the water on an eco-friendly electric boat.

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Become the captain of your own adventure! Navigate Sydney Harbour soak in stunning views of iconic landmarks and discover hidden beaches for a perfect day on the water.

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Want to see Sydney Harbour? Want to try sailing? Want to do it on a unique classic sailing yacht? This is your opportunity to sail on the iconic Sydney harbour on a stunning classic yacht. (starts from Barangaroo)

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Captain your very own electric picnic boat with no experience or boat license required. Sail Middle Harbour and explore Sydney from the water on an eco-friendly electric boat.

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Captain your own eco-friendly electric picnic boat for 3 hours through the scenic waters of Akuna Bay—no license required!

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Savor delightful moments on the water with friends enjoying good food and great company aboard a GoBoat while soaking in Sydney's stunning scenery. Relax unwind and connect with nature.

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The Best Sailing tours and Captained boat rentals in
New South Wales

Sailing Experience (2.5 hrs 24ft yacht)

Port Stephens 3 Hour Whale and Dolphin Watch Cruise

Learn to Sail on Sydney Harbour: Australian Sailing Start Crewing

Try Yachting (Southwinds/Manly)

Double Kayak Hire - 4 Hours

South Shore Open Sail from Kewalo Harbor Including Drinks

Yacht Charter - Luxury Yacht Calypso

GoBoat Sydney (Akuna Bay) - 2 Hour Electric Picnic Boat Hire (up to 8 people)

Taster Sailing Experience (1.5 hrs 24ft yacht)

Marine Discovery + Snorkeling Cruise - Port Stephens

1 Hour Rental Deluxe Double Sea Kayak

GoBoat Sydney (Cabarita) - 2 Hour Electric Picnic Boat Hire (up to 8 people)

Drive Yourself Boat Hire in Sydney Harbour

Try Yachting (Southwinds/Sydney)

GoBoat Sydney (Mosman) - 2 Hour Electric Picnic Boat Hire (up to 8 people)

GoBoat Sydney (Mosman) - 1 Hour Electric Picnic Boat Hire (up to 8 people)

GoBoat Sydney (Mosman) - 3 Hour Electric Picnic Boat Hire (up to 8 people)

GoBoat Sydney (Cabarita) - 3 Hour Electric Picnic Boat Hire (up to 8 people)

GoBoat Sydney (Akuna Bay) - 3 Hour Electric Picnic Boat Hire (up to 8 people)

GoBoat Sydney (Cabarita) - 1 Hour Electric Picnic Boat Hire (up to 8 people)