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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$95-$8,455
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$8,455
Kayaks
Who says you need a motor to have fun on the water?
$90-$95
Sailboats
Set sail with these traditional wind-powered boats
$295-$315
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$1,185-$8,455
Diving
Explore the ocean depths with trained boat operators
$160
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$295
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$325
Canoes
A classic option for leisurely paddling
$90
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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
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!
Nellie
Luxury Sailing at its Finest in the Bay of Islands and beyond
Scott is a fantastic captain and host! All of our expectations were exceeded! The boat and itinerary were top notch. We loved our time cruising in & around the Bay of Islands and can’t wait to book a return trip. Nothing compares to a few great days on the water with good friends and outstanding scenery.
AP
Annelle
Sailing Adventures, 33ft Sports Cruising Catamaran
I had booked the island hopper for a group of 7 ladies and couldn’t have asked for a more beautiful experience on the water! Our sailors Luke and Amy were so nice and super chill. They even let a few of us have a crack at steering the sail. Couldn’t recommend this enough
KR
Katw
Boat Hire on Sailing Catamaran with pro skipper (max 30 guests) on Gold Coast
steve, Thank you so much for accommodating our group so last minute. As you know, we are in town for a country music festival in ipswich and we’re so glad to spend our day off on the ocean. Obviously, we booked under our alias for confidential reasons. That being said, we want you to know the social investment of Kelsea alone is $30,000. Old dominion is an equally influential act. As you’ve already posted and tagged (without approval), we would like to arrange an agreement. Kelsea is willing to post one more instagram photo (1.1 million followers) and tag your company with the compromise that you offer a discount to your services. Looking forward to hearing back from you and thank you again for a great day. looking forward to a long relationship!
dM
daniel
Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat
Unforgettable experience Awesome sailing ⛵️
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!
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