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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$235-$1,990
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$405
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$930-$1,245
Fishing Charters
Let a captain do the driving while you do the fishing
$155
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$155
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Adam
Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat
If you’re looking for an unforgettable way to experience Sydney Harbour, look no further than Jeremy and his sailing yacht, Lollibee. My family and I recently made the trip all the way from San Diego, and sailing with Jeremy was, without question, the highlight of our visit. From the moment we stepped aboard, Jeremy welcomed us with warmth and professionalism, instantly putting us at ease. His deep knowledge of the harbor and its history made the journey not only scenic but also wonderfully informative. Whether we were gliding past the iconic Sydney Opera House or pausing to take in the majesty of the Harbour Bridge, Jeremy made sure we had the best vantage points and plenty of time to soak in the views. What sets Jeremy apart is his passion for sailing and his dedication to creating a personalized experience. He made every effort to accommodate our family, ensuring we were comfortable and engaged throughout the trip. He even let our kids try their hand at steering the yacht, making them feel like seasoned sailors. The Lollibee itself is a gem—beautifully maintained, spacious, and perfectly suited for a relaxing day on the water. Whether you’re a seasoned sailor or stepping aboard a yacht for the first time, Jeremy makes the experience feel effortless and magical. If you’re visiting Sydney and want a unique way to see this spectacular harbor, don’t miss the chance to sail with Jeremy on the Lollibee. It’s an experience my family and I will treasure forever. Thank you, Jeremy, for making our trip truly special!
AS
Alastair
Skippered Seawind Resort 1050 Catamaran Charter
We had a family event with 20+ adults and kids. It was the perfect day on the water with the Kiralee crew so helpful and attentive. The perfect Sydney day out
JP
Jacquelene
32' Sailing Yacht Trips In Te Mahia
We booked a sailing tour with Deb and Phil and had such a great time. Everything was perfect, the boat was beautiful, the scenery was stunning, and the mid-sail snacks were delicious! Phil was very knowledgeable and we had a great day. Highlight of our trip, could not recommend them highly enough!
Anastasia
Sydney Harbour Charter on SPELLBOUND a luxury 12m Sailing Catamaran.
Blodwen & team are amazing !!! Our christmas party is a 100% succesful even though there is a bit of a rain but that doesnt stop us ! The boat is amazing , clean , BBQ provided , the lounge area is fabulous .
AS
Alexandre
Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat
5-star sailing with Jeremy - recommend to anyone looking for a day at sea while in Sydney!
Perry
Sailing Sydney Harbour on Luxury Sailboat
Great sail on the harbor - got to see the yacht racing closeup after a pleasant lunch at Rose Bay
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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