Top 15 Tall Ship Sailing in the USA

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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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger

2.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

3.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

4.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

5.1.5 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

6.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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Windjammer Classic Sunset Sail from Camden, Maine

7.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

8.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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Windjammer Classic Day Sail from Camden, Maine

9.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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New York City: Sunset Sail Aboard a Schooner

10.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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Key West: Schooner Sunset Sail with Food & Drinks

11.Key West: Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail from Key West aboard the wooden schooner America 2.0 for a two-hour sunset outing. The crew serves alcoholic and non-alcoholic drinks plus a personal hors d'oeuvres plate as you pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Keep watch for dolphins, turtles, water birds, and the Green Flash.

“Amazing cruise. The crew were fantastic, the cruise very relaxing, and the setting sun beautiful to see. Many thanks, a perfect evening.”

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NYC: Sunset Sail Aboard Schooner Adirondack

12.NYC: Sunset Sail Aboard Schooner Adirondack

★★★★★★★★★★4.9 · 283 reviews · 2 hours · from $90

Meet the crew at Pier 62 and spend two hours aboard the 80-foot schooner Adirondack. You’ll sail past Battery Park, Ellis Island, and the Statue of Liberty as Manhattan lights up. One alcoholic drink is included, with nonalcoholic drinks available for purchase. Warm blankets, photo help, and friendly crew service add comfort.

“The staff was amazing. The sailboat was beautiful. The harbor was amazing. We got up close to the Statue of Liberty and everybody had a great time.”

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NYC Statue of Liberty Tall Ship Sail aboard Clipper City

13.NYC Statue of Liberty Tall Ship Sail aboard Clipper City

★★★★★★★★★★4.5 · 264 reviews · 1 hour 30 minutes (approx.) · from $68

Board Clipper City at Pier 17 for a 90-minute harbor sail past the Brooklyn Bridge, Ellis Island, Governors Island, and the Statue of Liberty. This is a scenic sailing experience, not a narrated sightseeing tour. The onboard bar serves drinks for purchase, and the crew may invite you to help with the sails.

“Beautiful view, great drinks, friendly and entertaining staff. Would definitely take any newcomers to nyc on this tour. Pro tip: get in line to board at least 20min before departure time”

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Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

14.Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

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

Meet the captain and crew at Aquarium Wharf for a 90-minute sail aboard the three-masted Schooner Pride. Help raise sails up to 84 feet, pass Fort Sumter and Castle Pinckney, and watch for dolphins. This is a relaxed harbor ride rather than a nonstop narrated tour, with drinks sold on board.

“We really enjoyed sailing on the schooner, the captain and his crew were wonderful and were willing to answer any questions we had. We had a fantastic afternoon sailing in the harbor and would highly recommend that tour.”

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Key West Sunset Sail Aboard Legendary Schooner Appledore

15.Key West Sunset Sail Aboard Legendary Schooner Appledore

★★★★★★★★★★5.0 · 251 reviews · 2 hours (approx.)

Set sail from Key West Historic Seaport aboard the classic wooden schooner Appledore for a 2-hour sunset trip. You can help raise the sails, enjoy beer, wine, champagne, cocktails, soda, and hors d'oeuvres, and hear sea stories from crew such as Joe, Josh, Christina, Andy, and Pablo. The boat carries no more than 36 people.

“We had a nice time and the crew did a great job with food and drinks. The sunset was very nice and the ship was beautiful. Not sure it was worth the fee, but a good time.”

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