Category Sailing

Sydney · SAILING

15 Sailing Trips in Sydney That Earn the Fare

25 reviewed

Sydney: Discovery Whale Watching Tour by Catamaran

Sydney: Discovery Whale Watching Tour by Catamaran - Darling Harbour meeting point and getting set up

1.Discovery Whale Watching Tour by Catamaran

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

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.”

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Sydney Harbour: Sunset Catamaran Cruise

Sydney Harbour: Sunset Catamaran Cruise - What You’ll See: 360° Harbour Views That Make Sydney Feel Close

2.Sydney Harbour: Sunset Catamaran Cruise

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

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”

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Luxury Sailing Cruise on Sydney Harbour with Lunch

Luxury Sailing Cruise on Sydney Harbour with Lunch - The Early Harbour Loop: Bridge, Opera House, Rocks, and Fort Denison

3.Luxury Sailing Cruise on Sydney Harbour with Lunch

★★★★★★★★★★5.0 · 171 reviews · from $251Top rated

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.”

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Sydney: Premium Catamaran Vivid Cruise with Welcome Drink

Sydney: Premium Catamaran Vivid Cruise with Welcome Drink - On the Whitehaven: seating comfort and the smaller-boat advantage

4.Premium Catamaran Vivid Cruise with Welcome Drink

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

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!”

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Vivid 90-Minute Sydney Harbour Catamaran Cruise with BYO Drinks

Vivid 90-Minute Sydney Harbour Catamaran Cruise with BYO Drinks - The 90-minute Vivid route: Harbour Bridge, Opera House, gardens, and more

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

Sydney Harbour: 2-Hour Morning Yacht Cruise with Morning Tea - The route in two hours: Bridge, Opera House, and the harbour edges

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes - Where you board: Pier 2, Walsh Bay (and how to not waste time)

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

★★★★★★★★★★5.0 · 37 reviews · from $53

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.”

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Sydney Harbour Sailing Experience

Sydney Harbour Sailing Experience - The meeting point and start time: getting on board without stress

8.Sydney Harbour Sailing Experience

★★★★★★★★★★4.5 · 32 reviews · from $118

3-hour small-group sail on Sydney Harbour with Opera House and Harbour Bridge views. Learn to raise sails on a 10-person yacht.

“Lots of fun learning to help sail, guide was excellent. Would definitely go again and recommend it to others”

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Private Catamaran Hire on Sydney Harbour

Private Catamaran Hire on Sydney Harbour - Your boat setup: toilet, swim ladder, speakers, and a galley

9.Private Catamaran Hire on Sydney Harbour

★★★★★★★★★★5.0 · 32 reviews · from $1,237

Private catamaran hire on Sydney Harbour with skipper, bridge and Opera House views, toilet and swim ladder, BYO food with BBQ option.

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

From Manly: Sydney Harbour Hands-On 2.5 Hour Yacht Cruise - Helping set sails (and steering) near Sydney’s landmarks

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

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

Hands-on yacht cruise from Manly: set sails, steer, and spot the Opera House and Harbour Bridge from Sydney Harbour in 2.5 hours.

“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.”

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Whale Watching Sailing Experience in Sydney

Whale Watching Sailing Experience in Sydney - Small-Group Sailing with Captain Doug and Crew Help

11.Whale Watching Sailing Experience in Sydney

★★★★★★★★★★5.0 · 28 reviews · from $71

A 3-hour small-group sailing whale watch from Rose Bay, cruising Sydney Harbour to Port Jackson and following humpbacks in the Tasman Sea.

“A great day all around. After finding four whales we followed them for quite some time. The Captain knew what pace they were travelling and was able to keep up with them even when they dived. A truly exhilarating experience.”

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Sydney Harbour – Sailing Hands-On Experience

Sydney Harbour - Sailing Hands-On Experience - Hands-On Sailing: What You Can Do Onboard

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes

Vivid 90-Minute Sydney Harbour Intimate Catamaran Cruise with Canapes - Where you board: Pier 2, Walsh Bay (and how to not waste time)

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

2 1/2 Hr Private Skippered Yacht Charter and Platter on Pittwater - What the yacht-and-skipper setup means for your comfort

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

★★★★★★★★★★5.0 · 15 reviews · from $261

Private 2.5-hr skippered Beneteau yacht on Pittwater from Palm Beach, with platter lunch and swimming stops at Portuguese Beach and The Basin.

“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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From Manly: Sydney Harbour Hands-On Taster Yacht Cruise

From Manly: Sydney Harbour Hands-On Taster Yacht Cruise - Meeting on the wharf: find Manly Yacht Club the easy way

15.From Manly: Sydney Harbour Hands-On Taster Yacht Cruise

★★★★★★★★★★4.9 · 13 reviews · 1h 30m · from $84

Hands-on Sydney Harbour yacht taster from Manly. Help set sails and steer in a small group. 90 minutes, $84.

“We had an awesome sailing trip with our skipper Onur, who made sure that we made a hands on experience, while giving a real sailing flavor and even provided a route that gave us spectacular views of the city. Highly recommend!”

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