The 15 Sailing Trips in Sydney to Book Before You Land

Cruises & Boat Tours, Sailing, Sydney Boat Charters, Sydney Whale Watching Cruises, Tour Reviews, Tours

Sydney: Discovery Whale Watching Tour by Catamaran

/ August 4, 2026

1.Discovery Whale Watching Tour by Catamaran

★★★★★★★★★★4.2 · 402 reviews · 2h 30m · from $63Our pick

A 150-minute Sydney whale watching cruise on a fast catamaran, reaching open ocean quickly for more sightings, with photo and drinks included.

“we did the afternoon whale watching cruise it was thought was so two of our four people backed out preferring to go milder seas it was hard to see any whales because it was so choppy we managed to find one who put on a bit of a display for us sadly all I managed to catch on my phone was four splashes the whales were just too fast for me couldn't hear the commentary over the booming seas The boat was adequate and seemed stable enough even in the larger waves so we could go quite a way out to find the whale activity”

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Cruises & Boat Tours, Evening Experiences, Sailing, Sydney Boat Charters, Tour Reviews

Sydney Harbour: Sunset Catamaran Cruise

/ August 4, 2026

2.Sydney Harbour: Sunset Catamaran Cruise

★★★★★★★★★★4.8 · 261 reviews · 1 hour · from $41Best value

Intimate 1-hour Sydney Harbour sunset cruise from Circular Quay on the Kirralee catamaran, with snacks, soft drinks, and BYOB.

“It was a lovely experience! The sunset was beautiful, and we managed to get some great photos. The crew was friendly and helpful, which made the trip even more enjoyable. Overall, a very pleasant outing. If I had one small suggestion, it would be to extend the trip by about 30 minutes so we could enjoy the scenery a bit more as it got darker. But honestly, it was exactly as advertised so I’m still giving it 5 stars!”

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Cruises & Boat Tours, Lunch Experiences, Sailing, Sydney Boat Charters, Tour Reviews, VIP

Luxury Sailing Cruise on Sydney Harbour with Lunch

/ August 4, 2026

3.Luxury Sailing Cruise on Sydney Harbour with Lunch

★★★★★★★★★★5.0 · 171 reviews · from $251.04Top rated

Luxury small-group yacht sail around Sydney Harbour with lunch, beer and wine, plus snorkel gear and time at Store Beach.

“David is an incredible host/guide. The sights, the sailing and swimming spot were all a highlight of our trip to Sydney.”

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Sydney: Premium Catamaran Vivid Cruise with Welcome Drink

/ August 4, 2026

4.Premium Catamaran Vivid Cruise with Welcome Drink

★★★★★★★★★★4.0 · 104 reviews · 1h 30m · from $63

Ride the 55ft Whitehaven catamaran for 90 minutes of VIVID Sydney harbor lights, with a welcome drink and space to move and photograph.

“Easy to find the ship - the landing stages are numbered - you just go to the number you are given. Warm welcome to the ship. Free drink and reasonably priced drinks to purchase. Good views of the harbour. We sat downstairs so not much interaction but enjoyed the experience!”

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Cruises & Boat Tours, Sailing, Sydney Boat Charters, Tour Reviews

Vivid 90-Minute Sydney Harbour Catamaran Cruise with BYO Drinks

/ August 4, 2026

5.Vivid 90-Minute Sydney Harbour Catamaran Cruise with BYO Drinks

★★★★★★★★★★5.0 · 56 reviews · from $42.32

A small catamaran cruise for 90 minutes of Vivid Sydney light shows, with BYO drinks and antipasto, plus close views of Opera House and Harbour Bridge.

“I chose this company because the boat is cool, only takes a small group and they had music playing softly, cold drinks and sandwiches. Will go again next year!”

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2-Hour Experiences, Cruises & Boat Tours, Morning, Sailing, Sydney Boat Charters, Tour Reviews

Sydney Harbour: 2-Hour Morning Yacht Cruise with Morning Tea

/ August 4, 2026

6.Sydney Harbour: 2-Hour Morning Yacht Cruise with Morning Tea

★★★★★★★★★★4.8 · 42 reviews · 2 hours · from $102

A 2-hour Sydney Harbour morning yacht cruise with tea, great bridge and Opera House views, and small-group storytelling.

“Graham was very informative. It was a very interesting trip.”

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Cruises & Boat Tours, Sailing, Sydney Boat Charters, Tour Reviews

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

/ August 5, 2026

7.Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

★★★★★★★★★★5.0 · 37 reviews · from $53.79

90-minute Vivid Sydney catamaran with canapes and a drink on Fleetwing II, cruising past Bridge, Opera House and Luna Park.

“Sydney harbour at night together with the Vivid lights is dazzling . An uncrowded & relaxed way to experience it. The canapes were generous & staff friendly.”

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Cruises & Boat Tours, Sailing, Tour Reviews

Sydney Harbour Sailing Experience

/ August 5, 2026

8.Sydney Harbour Sailing Experience

★★★★★★★★★★4.5 · 32 reviews · from $118.35

Small-group Sydney Harbour sailing on a yacht with hands-on help, big views of the Opera House and Bridge, about 3 hours.

“The skipper was very relaxed and made sure everyone on board was having a good experience. It was a great way to see parts of Sydney harbor that you can only get from a boat. Very memorable. Thanks.”

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Cruises & Boat Tours, Private, Sailing, Sydney Boat Charters, Tour Reviews

Private Catamaran Hire on Sydney Harbour

/ August 5, 2026

9.Private Catamaran Hire on Sydney Harbour

★★★★★★★★★★5.0 · 32 reviews · from $1,237.24

Private Sydney Harbour catamaran charter with flexible pickup, Harbour Bridge and Opera House passes, and time to anchor in a quiet cove.

“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”

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Cruises & Boat Tours, Sailing, Sydney Boat Charters, Tour Reviews, Workshops

From Manly: Sydney Harbour Hands-On 2.5 Hour Yacht Cruise

/ August 6, 2026

10.Sydney Harbour Hands-On 2.5 Hour Yacht Cruise

★★★★★★★★★★4.7 · 30 reviews · 2h 30m · from $119

Hands-on 2.5-hour yacht sailing from Manly, with small-group help steering and setting sails past Sydney Opera House and Harbour Bridge.

“excellent tour, we went on a very windy day and our guide was excellent guiding us through the details of sailing into a strong windy day”

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Cruises & Boat Tours, Sailing, Sydney Whale Watching Cruises, Tour Reviews

Whale Watching Sailing Experience in Sydney

/ August 6, 2026

11.Whale Watching Sailing Experience in Sydney

★★★★★★★★★★5.0 · 28 reviews · from $71.01

Small-group sailing whale watching from Rose Bay, Sydney Harbour views, sail when possible, and humpback whale sightings in the Tasman Sea May to November.

“What an amazing experience - Captain Douglas and First Mate Gavin got us right to the whales outside The Heads! We were saw 20-30 whales and 2 breaching!! Douglas was respectful of keeping our distance from the whales and ensured Read more”

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Cruises & Boat Tours, Sailing, Tour Reviews, Workshops

Sydney Harbour – Sailing Hands-On Experience

/ August 7, 2026

12.Sydney Harbour – Sailing Hands-On Experience

★★★★★★★★★★5.0 · 22 reviews · from $86.07

Hands-on sailing in Sydney Harbour on a small 24-foot keelboat from Manly, with safety gear and instruction included, 1.5 to 2.5 hrs.

“Diana was a great guide/ instructor. The 2 hour session was very educational and very active. I would recommend it to those who look to learn to sail.”

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Cruises & Boat Tours, Sailing, Sydney Boat Charters, Tour Reviews

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

/ August 8, 2026

13.Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

★★★★★★★★★★5.0 · 21 reviews · from $53.79

A 90-minute small-group catamaran cruise around Sydney Harbour for Vivid, with canapés, a drink, and great views of the Bridge and Opera House.

“Great views of the harbour - the bridge, the city and the Opera House! And wonderful way to enjoy the Sydney Vivid lights and friendly crew. Fun!”

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Cruises & Boat Tours, Private, Sailing, Sydney Boat Charters, Tour Reviews

2 1/2 Hr Private Skippered Yacht Charter and Platter on Pittwater

/ August 10, 2026

14.2 1/2 Hr Private Skippered Yacht Charter and Platter on Pittwater

★★★★★★★★★★5.0 · 15 reviews · from $261.57

Private Beneteau yacht charter on Pittwater with a skipper, platter lunch, swim stops, and big sights like 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”

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