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

The Best Sailing tours and Captained boat rentals in Sydney | Updated April 2025

Glide along the serene waters of Sydney's rivers surrounded by city views and lush landscapes. It's the perfect way to bond with loved ones or enjoy some peaceful time alone.

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

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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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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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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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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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The Best Sailing tours and Captained boat rentals in Sydney

Canoe Hire

Double Kayak Hire - 4 Hours

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

Taster Sailing Experience (1.5 hrs 24ft yacht)

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

Learn to Sail on Sydney Harbour: Australian Sailing Start Crewing

Try Yachting (Southwinds/Sydney)

Sailing Experience (2.5 hrs 24ft yacht)

Yacht Charter - Luxury Yacht Calypso

Drive Yourself Boat Hire in Sydney Harbour

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

1 Hour Rental Deluxe Double Sea Kayak

Try Yachting (Southwinds/Manly)