The World’s 15 Best Tall Ship & Sailing Harbour Cruises

1.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45Our pick

Sail Charleston Harbor aboard the Schooner Pride for dolphins, Fort Sumter, bridge views, and a relaxed 90-minute afternoon cruise.

“This was a great experience!! The Captain and his mates were wonderful! There was no commentary in the voyage, but it was not needed……it was a beautiful fall day, and the sun on your face and the wind in your hair was what made the voyage perfect!!”

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2.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35Best value

Review of Boston’s 90-minute tall-ship cruise, with skyline views, sail-raising, drinks, practical tips, value, and honest drawbacks.

“This is a great way to get out on the water and see the Boston skyline. We really enjoyed Captain Fredo and his crew. It was worth every cent to see my family enjoying themselves!”

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3.Auckland Harbour Sailboat Cruise Including Three Course Dinner

★★★★★★★★★★4.5 · 476 reviews · from $105

Sail Auckland’s Waitematā Harbour at sunset with a three-course dinner, skyline views, live commentary, and a friendly crew aboard a 50-foot yacht.

“An adventure with dinner on a lovely sailboat. We sailed and enjoyed the scenery while being looked after by our knowledgeable and friendly crew. A wonderful, low stress way to experience Auckland's harbor waterways.”

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4.Seattle Sailing Harbor Tour

★★★★★★★★★★4.5 · 473 reviews · 2 hours (approx.) · from $39

Sail Seattle’s Elliott Bay aboard a historic tall ship for skyline, Space Needle, and mountain views, with friendly crew and flexible afternoon departures.

“Excellent experience. Captain and were very friendly and attentive. Best experience of our entire vacation. The price was more than reasonable for a 2 hour sailing trip.”

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5.Harbour Sailing Cruise with 3-Course Dinner

★★★★★★★★★★4.5 · 319 reviews · 2h 30m · from $95

Review of Auckland’s 2.5-hour sailing dinner cruise, with a three-course meal, sunset harbour views, crew commentary, tips, and practical advice.

“Fantastic crew aboard, relaxed and engaging skipper and all around excellent experience - an “Aukland “must do”’!”

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6.Auckland Harbour 1.5-Hour Sailing Cruise

★★★★★★★★★★4.7 · 301 reviews · 1h 30m · from $65

Review of Auckland’s 90-minute harbor sailing cruise, with skyline views, hands-on sailing, crew commentary, refreshments, and practical tips.

“We had the best time ever. The crew were so professional and friendly guiding the trip brilliantly. We enjoyed steering the boat under the harbour bridge. A great experience - go on it and make memories.”

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7.Tall Ship Harbor Sail

★★★★★★★★★★4.6 · 261 reviews · 1h 30m · from $35

Sail Boston Harbor aboard a classic schooner for 90 minutes of skyline views, fresh air, optional drinks, and hands-on sailing for $35.

“Excellent trip and beautiful day for sailing. Crew was friendly and knowledgeable.”

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8.Schooner Sailing Harbor Tour & Dolphin Watch

★★★★★★★★★★4.6 · 255 reviews · from $48

Review of Charleston’s Schooner Pride harbor sail, with dolphin watching, Fort Sumter views, pricing, tips, and what to expect.

“The captain&crew were great, enjoyed the sail boat ride but wish it was longer .Also I wish there was a family option price ,it was expensive to pay for 8 family members .It was a surprise for my father’s birthday ,he is a sailor &loved being out on the water,relaxing while sailing along ..There was dolphins but not up close ,”

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9.Downtown Harbor Sailing Cruise

★★★★★★★★★★4.8 · 227 reviews · 90 minutes - 2 hours · from $66

Review of Boston’s Downtown Harbor Sailing Cruise, with route details, value advice, onboard tips, and what to expect aboard a classic schooner.

“Friendly and relaxed crew, weather was beautiful so made it even better”

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10.Tall Sailboat Sunset Harbor Cruise

★★★★★★★★★★4.8 · 223 reviews · 2 hours · from $79

Sail Seattle Harbor aboard the Bay Lady at sunset, with skyline views, optional sailing duties, onboard drinks, and Mount Rainier on clear days.

“We got lucky and the weather was fantastic. We enjoyed a beautiful sunset on the boat. The crew were really knowledgeable and extremely welcoming.”

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11.Luxury Sailing Cruise on Sydney Harbour with Lunch

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

Review of Sydney’s 5-hour luxury yacht cruise, with harbour landmarks, swimming, snorkeling, gourmet lunch, Australian wine, and a group of eight.

“Fantastic sail with Dave! Happens day was perfect with great winds, but Dave is a great captain and host. Lunch was truly out of this world good!! Wonderful way to see Sydney Harbour and to have a great tour along with that. Perfect Sydney day!!”

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12.JFarwell Adventure Yacht Sailing in the Halifax Harbour

★★★★★★★★★★5.0 · 147 reviews · 1 hour 30 minutes (approx.) · from $82

Sail Halifax Harbour aboard a small yacht, help raise the sails, steer the boat, and enjoy Nova Scotia views with JFarwell Sailing Tours.

“It is great! Not crowded and the Captain and crew are top notch and friendly. I have twenty three characters to ….”

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13.Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

★★★★★★★★★★4.5 · 126 reviews · 2 hours (approx.) · from $54

Review of Boothbay Harbor’s 2-hour Schooner Eastwind sail, with practical tips on weather, seating, crew, scenery, price, and family appeal.

“It was a windy fall day so make sure you bring a jacket under those circumstances otherwise dress accordingly”

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14.Sunset Tall Ship Harbor Cruise

★★★★★★★★★★4.8 · 115 reviews · 2 hours · from $68

Review of Boston’s sunset tall ship cruise, with sail raising, skyline views, onboard drinks, practical tips, access details, and value advice.

“this was an amazing cruise in the Boston harbor! I was traveling with family. My daughter and I asked the captain of we could steer the ship. the captain was so friendly and nice, allowing us a few moments to steer. we really enjoyed the beautiful views going at sunset. would definitely do this again!!”

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15.Tall Ship Harbor Cruise

★★★★★★★★★★4.7 · 86 reviews · from $73

Sail Seattle Harbor aboard the schooner Bay Lady for skyline, mountain, wildlife, hands-on sailing, and a relaxed two-hour cruise.

“Excellent time out on the water! The crew was very entertaining and made it exciting. We had the best time!!!”

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