Best Tall Ship and Schooner Sails: Our Top 15

Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

1.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Top of the fleet

Board the replica 1851 schooner America 2.0 at Key West Bight Marina for a relaxed two-hour sunset sail. Captains such as Janet, Rae, and Dan have guided recent trips, while the crew serves beer, wine, Champagne, soda, and plated hors d’oeuvres. You’ll pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse before returning to the marina.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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Toronto Tall Ship Boat Cruise

2.Toronto Tall Ship Boat Cruise

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

Sail Toronto Harbour aboard the historic Tall Ship Kajama, a 1930s three-masted schooner. Allow 30 minutes to board, then spend about 90 minutes on the water, helping raise the sails, hearing sea shanties, and viewing the skyline, Toronto Islands, and CN Tower. Food, drinks, and souvenir photos cost extra.

“Took my kids for my daughter's birthday. The staff was helpful and knowledgeable. The whole trip was lovely and we enjoyed every moment!”

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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

3.Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

★★★★★★★★★★5.0 · 668 reviews · 1 hour 30 minutes (approx.) · from $47

Meet the crew at Harbour Town and help turn your children into pirates with costumes, face paint, tattoos, pirate names, and lessons. Then sail the Black Dagger in search of treasure, read the map, battle Stinky Pete with water cannons, and return with loot. Scurvy and Ever are among the lively pirate characters you may meet.

“Excellent, safe trip. Actors and actress were top notch. Kids haven’t stopped talking about it since it ended!”

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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

Board the 84-foot Schooner Pride at Aquarium Wharf for a 90-minute, mostly quiet sail past Fort Sumter, Patriots Point, the USS Yorktown, Waterfront Park, and the Ravenel Bridge. The friendly crew may let you help raise the sails. Bring snacks, buy drinks on board, and watch for dolphins.

“Super relaxing and enjoyable My husband and I really enjoyed it. The crew was very nice and accommodating”

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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 $35Lowest fare aboard

Board the Liberty Star at Marina Overlook for a 90-minute Boston Harbor sail. Captain Fredo and crew may invite you to help raise the sails, while you enjoy skyline views, fresh air, snacks, and drinks, including South Boston beer. Bring a bagged lunch, but do not expect a fully narrated harbor tour.

“Beautiful views of Boston. Such a different experience from the water. The crew was great. Loved it!”

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1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

6.1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

★★★★★★★★★★4.0 · 601 reviews · 2 hours (approx.) · from $70

Board the Schooner Margaret Todd at Bar Harbor Inn Pier for a roughly two-hour sail through Frenchman Bay. You’ll pass the Porcupine Islands, view Acadia National Park from the water, watch for seals and eagles, and help raise the sails if conditions allow. Bring a jacket, arrive early, and expect a shared boat with up to 150 people.

“Relaxing and smooth sailing. Friendly staff and music was great. He sang all modern songs and I loved it.”

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Schooner Fame Sailing Tour

7.Schooner Fame Sailing Tour

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

You sail Salem Sound aboard Fame, a replica privateer schooner, for about 1 hour and 40 minutes. Captain Mike and the crew may invite you to raise the sails, steer, or help with the flag. Expect local history, views of the Salem coast, snacks and drinks for sale, and a cannon firing. Sunset trips are especially scenic but can turn cold.

“Absolutely recommend - the captain and crew were not only fun and engaging, but they were very kind and entertaining.”

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Sydney Harbour Tall Ship Twilight Dinner Cruise

8.Sydney Harbour Tall Ship Twilight Dinner Cruise

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

Meet at Campbells Cove in The Rocks for a twilight cruise aboard a restored tall ship. You’ll pass the Opera House, Harbour Bridge, Fort Denison, Taronga Zoo, Luna Park, and more while enjoying dinner and live commentary. Howard and Ruth are among the hosts mentioned for their warm storytelling. A mast climb is available for an extra fee.

“This is a friendly, relaxing and informative experience that takes you into the heart of Sydney and its beautiful harbour. The Captain, host and young crew were a delight, welcoming, and knowledgeable of the history of the harbour and tall ships. The meal was terrific and feel of the boat unforgettable. Accompanied by my adult daughter we had the best time together, catching up, feeling the breeze off the water and in the sails that brought us back to the dock. Thanks!”

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Windjammer Classic Sunset Sail from Camden, Maine

9.Windjammer Classic Sunset Sail from Camden, Maine

★★★★★★★★★★5.0 · 425 reviews · 2 hours (approx.) · from $64

Join Captain Sean and crew aboard the 86-foot Appledore II for a two-hour sunset sail from Camden Harbor. Help raise the sails, try the wheel, pass Curtis Island Light, and watch the sun set behind Mount Battie. Drinks are available to buy, blankets may be offered on cool evenings, and the ship returns to Bayview Landing.

“Attentive service. Great boat. Tips: use bathroom before leaving, there is a bathroom but of course it’s below deck! Get there early for the best side seats.”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

10.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★★★★★★★★★★4.5 · 414 reviews · 2 hours (approx.) · from $68

Spend about two hours aboard a Liberty Fleet tall ship, sailing from Fan Pier Marina around Boston Harbor at sunset. Expect skyline and island views, a relaxed crew, drinks and snacks for purchase, and occasional chances to help with the sails. Captains and crew members may vary, with Captain Fredo, Jess, and Max among the crew praised for making the trip fun.

“We had a wonderful time on the sunset cruise! The crew was very knowledgeable and kind. They were very attentive with refilling drinks! We would definitely do this again the next time we are in the Boston area! Highly recommend!”

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Sydney Harbour: Tall Ship Afternoon Cruise

11.Sydney Harbour: Tall Ship Afternoon Cruise

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

Spend 90 minutes aboard an 1850s-style wooden tall ship, sailing past the Opera House, Fort Denison, and under Harbour Bridge. You can help with ropes, sails, or steering, while English-speaking hosts such as Ruth and Jim share Sydney stories. Drinks are available to buy, and mast climbing costs extra.

“good time to explain and visitors could participate in running the ship ⚓”

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Windjammer Classic Day Sail from Camden, Maine

12.Windjammer Classic Day Sail from Camden, Maine

★★★★★★★★★★5.0 · 406 reviews · 2 hours (approx.) · from $59

Spend about two hours aboard the wooden schooner Appledore II, sailing from Camden’s Bayview Landing into Penobscot Bay. The crew may invite you to help raise the sails or take the wheel, while captains such as Sean and Pablo share stories about the ship and coast. Drinks, restrooms, wide decks, and multiple daily departures make this an easy Maine outing.

“Captain Sean, deck hands Andy and Mary were super nice! They answered all of our questions without sounding condescending. The Appledore II was comfortable to ride on. I even got to help raise the sails. Excellent experience!”

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

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

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

Spend 5.5 hours aboard the working schooner R. Tucker Thompson, sailing from Russell through the Bay of Islands. Help with ropes, steer the ship, climb the rigging, swim from the boat, and visit an island viewpoint. Morning tea, scones, chicken BBQ lunch, and optional Paihia to Russell ferry transport are included.

“A fantastic experience. Our son loved the wild weather, the ability to help on the boat and the crew where incredibly. Highly recommend for everyone.”

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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

14.Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

★★★★★★★★★★5.0 · 360 reviews · 7 hours (approx.) · from $169

Spend about seven hours sailing from Alghero with Colin and Rachel aboard the traditional wooden Andrea Jensen. See Capo Caccia’s cliffs, swim and snorkel in a secluded bay, enjoy a freshly prepared two-course lunch with wine and beer, then sail back beneath the ship’s red sails.

“We spent a absolutely superb day on this very lovable boat. The crew were a pleasure to be with and as English speaking owners made the day that little easier. The food and drink which was excellent were offered without hesitation. The company of limited numbers on board added to the free spirit of the day. Colin, Rachel and Constance their little helper. Thank you for a wonderful day. David & Amanda 27 Aug 2020”

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New York City: Sunset Sail Aboard a Schooner

15.New York City: Sunset Sail Aboard a Schooner

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

Spend two hours aboard the 105-foot Schooner America, sailing from Chelsea Piers down the Hudson to Ellis Island and the Statue of Liberty. You get one beer, wine, or Champagne if you are 21 or older, plus a professional crew and wide harbor views. Bring a warm layer, arrive early, and expect a relaxed rather than fast-paced cruise.

“The tour was excellent!! Shanon the captain and the crew, Colin and Grant were great!! I would definitely do this tour again and recommend to others!!”

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