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The World’s 15 Best Tall Ship and Schooner Sailings

40 sailing trips  ·  from $12 a head

Gaff rigs, wooden decks and a crew that will hand you a rope. These 15 old boats are compared on how much sailing you do yourself, how long the trip runs and what it costs to stand on a hundred-year-old deck.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The early route: Fort Zachary and the Key West shore
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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Toronto Tall Ship Boat Cruise - Raising the sails with the crew
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Toronto Tall Ship Boat Cruise

2.Toronto Tall Ship Boat Cruise

★★★★★★★★★★4.5 · 676 reviews · 2 hours (approx.) · from $38

Review of Toronto’s Tall Ship Kajama cruise, with skyline views, sail raising, sea shanties, food, timing, value, and practical tips.

“It was good and the only thing that could be improved would making the trip longer. I would limit the volume on purchasing booze. The whole boat knew their life stories of 2 girls and 2 guys”

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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger - Sailing Along Hilton Head’s Coastline
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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - Fort Sumter and the story of Charleston Harbor
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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

4.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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

Review of Charleston’s 90-minute Schooner Pride dolphin cruise, with Fort Sumter, harbor views, sailing tips, pricing, and honest drawbacks.

“Was an amazing experience will do that again, the ship and the crew was amazing and so helpful allowing people to help raise the sails. What a great service and experience.”

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Classic Tall Ship Cruise in Boston Harbor - Setting Sail on the Liberty Star
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Classic Tall Ship Cruise in Boston Harbor

5.Classic Tall Ship Cruise in Boston Harbor

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

Sail Boston Harbor aboard a classic schooner for skyline views, helpful crew, drinks, and a relaxed 90-minute outing.

“It was a great trip, plenty of wind for a good sail. The crew was informative, attentive and lots of fun!”

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Schooner Fame Sailing Tour - Raising sails, steering, and firing the cannon
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Schooner Fame Sailing Tour

6.Schooner Fame Sailing Tour

★★★★★★★★★★5.0 · 571 reviews · 1 hour 40 minutes (approx.) · from $50

Sail Salem Sound aboard the replica privateer schooner Fame, help raise the sails, hear local history, and enjoy a hands-on cruise for $50.65.

“The crew so nice, let you steer schooner and very informative. Had a great time today! Definitely recommend this excursion.”

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Sydney Harbour Tall Ship Twilight Dinner Cruise - What the dinner adds to the evening
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Sydney Harbour Tall Ship Twilight Dinner Cruise

7.Sydney Harbour Tall Ship Twilight Dinner Cruise

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

Review the Sydney Harbour Tall Ship Twilight Dinner Cruise, with landmark views, dinner, history, practical tips, value, and honest drawbacks.

“Was a wonderfull experience i think 2 hours was a bit to long as the kids were getting restless the last half an hour. But the dinner was amazing and filling The tour guide was funny knowledgeable.”

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Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour - Starting on the upper deck
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Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour

Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Boston Harbor at sunset, from the deck
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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Sydney Harbour: Tall Ship Afternoon Cruise - A wooden tall ship instead of a standard harbor boat
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Sydney Harbour: Tall Ship Afternoon Cruise

Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch - Starting at Russell Wharf
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Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

11.Bay of Islands Tall Ship Sailing on R. Tucker Thompson Including BBQ Lunch

★★★★★★★★★★5.0 · 361 reviews · from $111

Sail the Bay of Islands aboard the R. Tucker Thompson with scones, BBQ lunch, island stops, rope swings, and hands-on tall-ship fun.

“The day was perfect. I have mobility issues and from the first moment, the crew were there to help; willingly and graciously. Our crew, led by captain Magnus were super friendly, interactive (my husband helped sail) and above all fun! Fresh-baked scones with ham and whipped cream were served with coffee and tea. Followed by a stop at an island to swim and explore. Lunch of BBQ chicken, salad, fresh breads and butter, potato salad were waiting for us back on board. The sailing ship was a beautiful adventure and each of our 4 said it was beyond expectations, which were high! Don’t miss this…such value for your money and…”

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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine - A secluded bay for swimming and snorkeling
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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

New York City: Sunset Sail Aboard a Schooner - Sailing South Along the Hudson River
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New York City: Sunset Sail Aboard a Schooner

13.Sunset Sail Aboard a Schooner

★★★★★★★★★★4.9 · 344 reviews · 2 hours · from $101

Sail into a New York sunset aboard the Schooner America, with Statue of Liberty views, a complimentary drink, and a polished crew.

“This sailing was the perfect activity to end our trip to New York. It was very relaxing and beautiful to see the sunset over the skyline, the Statue of Liberty, and the night lights as we returned to port.”

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Sydney: Tall Ship Harbour Twilight Dinner Cruise - From Campbell’s Cove to open harbour views
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Sydney: Tall Ship Harbour Twilight Dinner Cruise

14.Tall Ship Harbour Twilight Dinner Cruise

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

Review of Sydney’s two-hour tall ship twilight dinner cruise, with harbour views, a three-course meal, sailing activities, price tips, and practical advice.

“Bloody amazing! Would recommend anyone visiting Sydney to go and have the experience. Crew are bubbly, bright and happy to talk (when able 🙂) Night time is the best, awesome photos avaliable throught the trip!”

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Key West: Schooner Sunset Sail with Food & Drinks - America 2.0 brings the right kind of drama
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Key West: Schooner Sunset Sail with Food & Drinks

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