Sydney · SAILING
Good sailing trips fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.
Board Fantasea Avalon at Aquarium Wharf in Darling Harbour for a 150-minute whale-watching cruise. The purpose-built catamaran reaches open water in about 30 minutes, with air-conditioned cabins, two viewing levels, complimentary hot drinks and water, and an onboard photographer.
“Service staff very patience and polite. Treat safety seriously.”
Board the catamaran Kirralee at Man O'War Steps beside the Opera House for a 1-hour sunset loop around Sydney Harbour. With up to 30 passengers, outdoor viewing nets, indoor shelter, a grazing platter, and BYO alcohol, you get an easygoing evening with views of the Opera House, Harbour Bridge, and Darling Harbour.
“Beautiful views of Sydney and the opera house. Great snacks. Wish they had more water than pop.”
Join Captain David aboard the 40-foot yacht Emma Mei for five hours on Sydney Harbour. Sail beneath the Harbour Bridge, pass the Opera House and Watsons Bay, then anchor at Store Beach for lunch, swimming, snorkeling, or quiet time on deck. Groups are limited to eight.
“Visiting our adult daughter in Melbourne and spending a week in Sydney. We all thoroughly enjoyed our day sailing on the harbor. Dave and Emily were lovely. Both knowledgeable and tons of fun. Views were spectacular, lunch was fantastic. Highly recommend this one!”
Spend 90 minutes aboard Whitehaven, a 55-foot catamaran capped at 70 passengers. You will see Vivid Sydney lights, the Opera House, Harbour Bridge, and city waterfront from indoor or outdoor seats, with a welcome drink and optional snacks and drinks onboard.
“It was really good. My both kids enj8yed alot. They danced 💃 on the cruise.”
Board the 35-foot catamaran Kirralee at Pier 2, Walsh Bay for a 90-minute Vivid Sydney cruise. An experienced skipper and host guide you beneath the Harbour Bridge, past the Opera House, Gardens, Barangaroo, and Darling Harbour. Bring your own alcohol, enjoy antipasto, and take in the lights from a small group setting.
“Such a nice cruise around the harbour, and a nice antipasto & beverage is provided. Would suggest for a couple that are spending some time in Sydney”
Start at Circular Quay for a two-hour morning yacht cruise with a small group, coffee, tea, juice, and light refreshments. Your English-speaking captain and host point out the Harbour Bridge, Opera House, Fort Denison, bays, coves, waterfront homes, and Bondi Beach. Hosts have included Maggie, Graham, Jake, and Captain Charlie.
“Really enjoyed this yacht cruise. The guides are very informative and amusing. Ship is nice and comfortable. Only 5 guests on this cruise ride so we feel it’s a great value for money.”
Board Fleetwing II at Pier 2, Walsh Bay, for a 90-minute evening cruise during Vivid Sydney. You’ll pass the Harbour Bridge, Opera House, Circular Quay, Luna Park, Barangaroo, and Darling Harbour, with canapes and one beer, wine, soft drink, or juice included.
“My friends and I have a memorable experience, one we won’t forget. The staff were friendly and welcoming. Would definitely recommend the experience to anyone.”
Take a private catamaran around Sydney Harbour with an experienced skipper and deckhand. Cruise beneath the Harbour Bridge, pass the Opera House, anchor in a quiet cove, swim, play your music, and bring your own food and drinks. Pickup and drop-off points can be arranged around the harbour.
“Friday was a truly wonderful experience onboard The Kirralee smoothly motoring around our most amazing backdrop of Sydney Harbour. Perfect weather, perfect Company, beautiful boat with a terrific crew of two. I cannot recommend this eRead more”
Join a small yacht crew at King Street Wharf for a roughly three-hour Sydney Harbour sail. You can help raise sails, work the ropes, and pass the Opera House, Harbour Bridge, Fort Denison, Rose Bay, Vaucluse, and Kirribilli House. The yacht carries up to 10 people.
“Do not expect 3 hrs of sailing, despite the description. We motored the first 45 and the last 30 minutes. Bring your own food, as none is provided.”
Join an English-speaking skipper for 2.5 hours on Sydney Harbour with no more than four people aboard. From Manly, you can help set the sails, learn basic sailing, steer the yacht, and view the Opera House, Harbour Bridge, beaches, and waterfront homes when weather allows.
“As we had no prior sailing experience, our guide Will walked us through the basics of how sailing works. Gradually, we were able to take part in operating the boat ourselves, which was a lot of fun. We thoroughly enjoyed the experience and would highly recommend it to anyone with little or no sailing experience.”
Join Douglas, Sharon, or Gavin aboard a small sailing boat from Rose Bay for a three-hour whale-watching trip. You’ll cruise Sydney Harbour, head through Port Jackson into the Tasman Sea, and look for humpback whales in a group limited to 12 people. Sailing depends on conditions.
“Fantastic experience, the crew went out of their way to make sure we were comfortable, & saw Whales.”
Join Manly Sailing for a small-group sail on Sydney Harbour aboard a 24-foot keelboat. Your skipper, including instructors such as Will, George, or Diana, can teach you to steer, set sails, and handle basic sailing tasks, or let you simply enjoy the ride.
“We picked the best day to learn to sail, the weather was perfect. Will & George were great teachers, I would highly recommend this experience to others.”
Cruise Sydney Harbour for 90 minutes aboard Heaven, a multi-level catamaran limited to 40 people. You’ll pass the Opera House, Harbour Bridge, Luna Park, Circular Quay, and Darling Harbour while enjoying roaming canapés and one complimentary drink. Skipper Frank may add local stories along the way.
“Our boat was Heaven! And lived up to its name! What an unforgettable adventure! Our skipper was Frank and his staff were warm and inviting! The hors d’oeuvres were very nice and the presentation lovely. Frank was top notch even taking Read more”
You’ll spend 2.5 hours on an exclusive Beneteau yacht from Palm Beach Wharf, with a skipper at the helm and lunch served aboard. Choose seafood, cold meats, vegetarian, or cheese and antipasto platters, then swim, visit The Basin, or cruise past Barrenjoey Lighthouse.
“A unique experience to see the beauty of Sydney’s landscape and waterways. Our skipper was warm, friendly and very knowledgeable about the area. He took us into a hidden cove where we could swim in the gorgeous turquoise waters. TRead more”
Join an English-speaking captain, with instructors such as Onur or Izzy, for a small-group sailing lesson from Manly. You can help set the sails and steer while cruising past northern Sydney beaches, coastal homes, and harbour views. The yacht holds no more than four participants.
“Our Instructor Onur was very good, patient and did a great job of explaining things.”
Pick a wharf, a lookout or a cellar door.
