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Sailboats
Set sail with these traditional wind-powered boats
$255-$1,390
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$255-$1,390
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$1,150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$195
Fishing Charters
Let a captain do the driving while you do the fishing
$1,150
OS
Oskar
Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat
Boat is gorgeous and intimate. Couldn’t have asked for more in terms of communication, flexibility and approachability with a plan that didn’t suit the normal mould. Jeremy was wonderful, professional and accomodating which allowed for one of the most memorable experiences of my life so far. Thanks!

Darlene
Set Sail on Sydney Harbour | 28ft SuperSonic MKII Sailboat
Jeremy was so patient and kind and understanding with us as it was our first time going on a yacht, the trip was a bit limited due to wind conditions but it was a unique experience with beautiful views and great for getting some nice shots on camera.

Nellie
Skippered and Crewed Charters aboard a Bali 4.5 - Bay of Islands, New Zealand
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

Roger
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.
CM
Chris
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
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!