10 Sydney Sailing Tours, Best Day First

1.Sydney Harbour Tall Ship Twilight Dinner Cruise

★★★★★★★★★★4.5 · 451 reviews · from $63Our pick

Meet at Campbells Cove in The Rocks for a twilight dinner cruise aboard a restored tall ship, sometimes the 104-year-old Southern Swan. Enjoy dinner, live commentary from hosts such as Howard or Ruth, and views of the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, Luna Park, and more. Mast climbing costs extra.

“Sitting out on the deck of a three mastered tool ship nibbling canapés and sipping bubbles. There is no better way to experience Sydney Harbour and it’s very best.!”

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2.Tall Ship Afternoon Cruise

★★★★★★★★★★4.6 · 412 reviews · 1h 30m · from $48Best value

Spend 90 minutes aboard an 1850s-style wooden tall ship with an English-speaking crew. Help raise the sails, try the helm, hear Sydney stories from guides such as Ruth and Jim, and pass the Opera House, Fort Denison, and Harbour Bridge. Snacks and drinks are available onboard, but mast climbing costs extra.

“We really enjoyed the cruise. The kids had great fun helping with the sails and looking round the ship.”

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3.Tall Ship Harbour Twilight Dinner Cruise

★★★★★★★★★★4.4 · 342 reviews · 2 hours · from $77

Join the Southern Swan or Soren Larsen at Campbell’s Cove for a two-hour twilight sail past the Opera House, Harbour Bridge, Fort Denison, and Luna Park. You can help set the sails, steer the ship, or relax with dinner. The English-speaking crew share harbour and ship stories, with drinks and mast climbing sold separately.

“fab trip, great hosts , good food and great that guests could contribute to trip”

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4.Sydney Harbour Tall Ship Afternoon Discovery Cruise

★★★★★★★★★★4.5 · 293 reviews · from $49

Board at Campbells Cove in The Rocks for a 90-minute tall ship cruise past Sydney’s top harbour sights. Crew members such as Jim, Ruth, Howard, and Captain James share maritime stories, help you raise the sails, and keep the trip lively. Snacks are included, while drinks and a mast climb cost extra.

“Staff was personable and insightful. Crew encouraged people to help when raising the sails. Felt comfortable and relaxed. Very pleasant time!”

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5.Tall Ship Vivid Dinner Cruise

★★★★★★★★★★4.4 · 272 reviews · 1h 30m · from $65

Cruise Sydney Harbour aboard the Soren Larsen or Southern Swan during Vivid Sydney. You’ll see the Opera House, Harbour Bridge, Circular Quay, and other illuminated waterfront sites from the water, with dinner, wine, or fruit juice included. Guides such as Howard add ship history, while the open deck gives you room to move and take photographs.

“Great night maybe a little more clearer commentary as space is limited. Thanks”

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6.Luxury Sailing Cruise on Sydney Harbour with Lunch

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

Meet Captain David at Darling Harbour for a five-hour cruise aboard the 40-foot yacht Emma Mei. Expect Sydney landmarks, local stories, a gourmet lunch with beer and wine, and free time to swim, snorkel, stroll, or relax at Store Beach. Groups are limited to eight.

“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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7.Tall Ship Lunch Cruise

★★★★★★★★★★4.8 · 69 reviews · 2 hours · from $77

Spend two hours aboard a traditional timber tall ship with an English-speaking crew. You’ll pass Sydney’s top harbour sights, help hoist the sails, and enjoy a freshly prepared three-course lunch. Crew members such as Howard, Ruth, and skipper Marti add local stories and a friendly nautical touch. Drinks and the optional mast climb cost extra.

“A fantastic event with a knowledgeable and very friendly crew. Ruth was great guide and a fountain of knowledge. Our lunch was really tasty and the warm chocolate brownie was amazing - my compliments to the chef! And to sail back up to the opera house was just idyllic! Thanks to you all.”

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8.Sydney Harbor Tall Ship Wine & Canapés Evening Cruise

★★★★★★★★★★5.0 · 3 reviews · 2h 30m · from $105

Spend 150 minutes aboard an 1850s-style tall ship, sailing from Campbell’s Cove past the Opera House and Harbour Bridge. Enjoy freshly prepared canapés, Australian wines, and bubbly while a live acoustic musician plays. On suitable evenings, you may help raise the sails, steer, or take part in sailing the ship. Adults only.

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9.Private Sunset Sail

★★★★★★★★★★5.0 · 2 reviews · 2 hours · from $601 whole boat, up to 10

Join Eastcoast Sailing for a private two-hour sunset cruise on a 38-foot catamaran. You’ll pass the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, and waterfront homes while enjoying snacks, soft drinks, music, and your own alcohol. The crew speaks English and provides glasses and safety gear.

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10.Sydney Harbor Tall Ship Convicts, Castles & Champagne Tour

★★★★★★★★★★5.0 · 2 reviews · 3 hours · from $84

Spend three hours aboard a traditional vessel with guides James and Esther, sailing past Sydney Harbour landmarks before a guided walk on convict-era Goat Island. Lunch includes butter chicken or vegan Goan curry, salads, brownie, bubbly, juice, and water. Meet at Campbell’s Cove Jetty.

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