The Best Sailboat Rentals in Sydney

Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat

We had an unforgettable trip with Jeremy. I highly recommend him and his boat. We always felt very safe with Jeremy in charge and he showed amazing flexibility to move the time of our trip due to expected bad weather. I got engaged to my girlfriend whilst on the boat he helped with the planning and photography at every stage making it truly memorable. He had a great cool box to keep the champagne cold. On the trip as we were heading back the wind suddenly picked up but Jeremy calmly got us back safely. Next time we are in Sydney we will be booking again with him

Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat

What a wonderful experience sailing with Jeremy in Sydney Harbor! From start to finish the views are spectacular, and sailing under the Harbor Bridge and by the Opera House was awesome. Additionally, Jeremy provided a beautiful lunch and refreshments! Finally, I experienced sailing the boat out towards the North Head with the views of the Pacific Ocean. I highly recommend Sailing with Jeremy.

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!

Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat

Jeremy was great and would recommend him to all

Skippered Seawind Resort 1050 Catamaran Charter

Frank was so accommodating. I really enjoyed him and he went out of his way to make our entire experience perfect! His experience really showed in his ability to position the boat in the perfect spot and knew where the best views were in the harbour.

Sailing Sydney Harbour onboard Seawind Sailing Catamaran

We had an excellent trip with Carlo who took me and wife around Sydney Harbour and Rose Bay for our wedding anniversary. He helped cook our food and made the day special for us. The boat was clean and had all the necessarily facilities, including a lilypad and a stand up paddle-board to use