Sydney · TALL SHIP & SAILING CRUISES
14 reviewed
The shortlist to hand a friend flying in: the 14 tall ship & sailing cruises worth booking, each with its price, its rating, and the one thing to know before you commit.
Sail Sydney Harbour on a restored tall ship at twilight with a built-in dinner and live onboard storytelling past key landmarks.
“Loved it! A very enjoyable way to spend Christmas Eve! Food was great! Staff were wonderful. A lovely couple of hours”
Sail Sydney Harbour on a historic tall ship. Help set the sails, pass the Opera House and Harbour Bridge, and enjoy snacks for $48.
“We really enjoyed the cruise. The kids had great fun helping with the sails and looking round the ship.”
Sydney whale watching on a custom catamaran from Darling Harbour. Reach open ocean fast, enjoy decks, drinks, onboard photos, 150 min.
“The seas were rough but the captain and all the crew warned everyone about the rough seas before departing, and handed sea sick bags out. The captain did at one point say the seas were too rough and we were heading back in when we spotted some whales. It was wonderful to see a two calfs, two moms and an escort whale. One of the mamma whales used her tail to hit the water giving us a hint that we should not be so close to her baby. When in Sydney will take another tour with them.”
Sail Sydney Harbour at twilight on a restored tall ship, with a three-course dinner and optional hands-on sail help.
“Stunning sunset sail with friendly and great local history”
Sail a historic tall ship on Sydney Harbour. Enjoy stories, snacks, and iconic views of the Opera House and Bridge, plus an optional mast climb.
“I was a bit late and couldn't find the pier so I literally missed the boat!! Oh well, I took a ferry ride and it was great!”
Tall ship dinner cruise for Vivid Sydney, 90 minutes on the harbor with Opera House light show views, meal and wine included.
“Fabulous night out. Great food, good choice of beverages, friendly staff. Really good value for money. And we were also lucky it was a warm, clear night to watch Vivid. Thoroughly recommend”
1-hour sunset catamaran on Sydney Harbour from Circular Quay. Small group, 360° views, snacks, and BYO alcohol.
“10/10 experience. Lovely cruise experience, everything was smooth, the crew made sure we had a great time and a smooth sail. They were helpful and patient with everybody taking photos and the snacks were a great finishing touch to an overall brilliant cruise. Highly recommended”
A small-group luxury sail on Sydney Harbour with a stop at Store Beach for swimming, snorkeling, and a gourmet lunch with beer and wine.
“The cruise was amazing from start to finish. Beautiful boat, wonderful information and conversation, fantastic lunch--can't think of one thing I didn't like about it other than when it ended. We were in Australia for 2 weeks and did lots of things, but this is one of the highlights I tell my friends and family about when they want to know about our trip.”
Sail a restored 1920s tall ship on Sydney Harbour for a 2-hour lunch cruise with great views, hands-on crew moments, and optional drinks.
“Fabulous! Great crew, great boat, good food and drinks, lively fellow shipmates. Weather was iffy but so glad we did it.”
90-minute Whitehaven catamaran cruise for Vivid Sydney from Darling Harbour with a welcome drink and Harbour Bridge/Opera House views.
“Couldn’t recommend highly enough if you are in Sydney when vivid is on. Book this cruise we will be doing this annually from now on. The staff were so friendly are really looked after us, boat was spacious with very comfy seating a truly amazing night out!”
Sail past Sydney Opera House and Harbour Bridge on a traditional tall ship lunch cruise, with sail-hoisting hands-on fun and a three-course meal.
“great experience. The crew were welcoming and knowledgeable with the history of the tall wooden boats in the harbour, the surrounding landscape past and present. It was nice to meet the owners and learn about their journey from europe with the tall wooden ship. i would highly recommend taking the tour fun for all ages.”
Small-group 90-minute Sydney Harbour catamaran for Vivid lights from Pier 2 Walsh Bay, with antipasto and BYO drinks.
“Fantastic. Crew were great. Whole trip was lovely. Food,boat & hospitality amazing. Nothing negative to say”
2-hour Sydney Harbour morning yacht cruise with coffee and tea. See the Bridge, Opera House, Bondi and Fort Denison.
“Graham was very informative. It was a very interesting trip.”
See Vivid Sydney lights from Fleetwing II on a cozy 90-minute catamaran with canapes, one drink, and easy harbor views.
“Our uber driver drop us off at the wrong location so we missed our scheduled cruise. The tour operator called and re scheduled us on the next cruise. Thank you for the reaching for us and accommodating us as well. Good spread of canapes and In house music can be add during the cruise. Thank you.”
