TALL SHIP SAILING IN THE USA

15 Tall Ship Sailing in the USA to Get on the Water

55 sailings  ·  from $35 a head

Wind, season and head-count decide more about a day afloat than the brochure does. These 15 tall ship sailing in the USA are set out with the hours, the price and the swim stops so the choice takes a minute.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The marina meeting point and boarding routine
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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 $122Our pick

Board America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

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Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger - Key details before you book
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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 set sail aboard the Black Dagger for a 90-minute pirate show made for families. Kids receive pirate names, face paint, temporary tattoos, costume gear, and lessons from characters such as Scurvy and Captain Kaitlyn. They follow a treasure map, battle Stinky Pete with water cannons, and take home a share of the loot.

“We loved it all! It was very interactive, and the kids had a great time! Ever did a great job, thank you guys!”

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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - What the non-narrated format really means
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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

Spend 90 minutes aboard the 84-foot Schooner Pride, a real sailing ship that uses wind power when conditions allow. The crew raises the sails, answers questions, and may let you help with the lines. Look for dolphins, Fort Sumter, the USS Yorktown, the Battery, and the Ravenel Bridge. Snacks are welcome, but drinks must be purchased on board.

“It was so fun! They really give you the experience you signed up for. We saw dolphins and they provided drinks and a few snacks as well.”

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Classic Tall Ship Cruise in Boston Harbor - Boarding at Marina Overlook
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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 $35Best value

Board Liberty Fleet of Tall Ships at Marina Overlook for a 90-minute sail aboard the Liberty Star. Captain Fredo and crew may invite you to help raise the sails while sharing harbor commentary. Bring a bagged lunch, buy drinks onboard, and enjoy skyline and Constitution views from the water.

“I enjoyed it. even go to help pull up the main sail!! Would love to do it again, actually go to get involved and do some of the tasks.”

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Schooner Fame Sailing Tour - What happens after you meet at Pickering Wharf
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Schooner Fame Sailing Tour

5.Schooner Fame Sailing Tour

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

Spend about 1 hour 40 minutes sailing Salem Sound aboard the replica privateer schooner Fame. From Pickering Wharf Marina, you can help raise the sails, steer, fold the flag, and hear stories about Salem’s privateers, pirates, and merchant ships. Captain Mike and the crew keep the trip friendly and hands-on. Drinks, snacks, blankets, and a cannon firing may add to the fun.

“It was a great experience. The captain and crew asked for volunteers to hoist the sails, steer the ship and at the end, fold the flag. It does get cold in the evening, so a sweatshirt is advisable, however they do provide blankets.”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Two hours of sailing, not a landmark lecture
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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

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

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

Board at Fan Pier Marina for a two-hour sunset sail aboard a classic Boston tall ship, often the Liberty Star. Expect skyline and harbor views, a relaxed crew, drinks and snacks for purchase, and possibly a chance to help with the sails. Capt. Fredo, Jess, and Max have worked some recent departures.

“The crew was fantastic. The views were amazing and drinks were good. Everyone onboard was having a great time. If you have never been on a tall ship this is a nice experience.”

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New York City: Sunset Sail Aboard a Schooner - Boarding at Pier 62 in Chelsea
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New York City: Sunset Sail Aboard a Schooner

7.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 past Ellis Island and the Statue of Liberty. You get one beer, wine, or Champagne if you are 21 or older, plus a polished crew and wide harbor views. Captain Shannon and crew members Colin and Grant have earned special praise, though you should bring a warm layer.

“The trip was great, but there was no champagne. No issue for me, as I prefer wine, but it should still be changed in the description.”

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Key West: Schooner Sunset Sail with Food & Drinks - Checking in behind Schooner Wharf Bar
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Key West: Schooner Sunset Sail with Food & Drinks

8.Schooner Sunset Sail with Food & Drinks

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

Sail for two hours aboard the America 2.0, a polished wooden schooner with teak decks and 3,600 square feet of canvas. Enjoy drinks and a personal hors d’oeuvres plate while the crew sails past Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Captain Janet is a favorite on many departures.

“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”

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NYC: Sunset Sail Aboard Schooner Adirondack - Sunset, skyline, and the changing light
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NYC: Sunset Sail Aboard Schooner Adirondack

9.Sunset Sail Aboard Schooner Adirondack

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

Meet the crew at Pier 62 for a two-hour evening sail aboard the 80-foot Schooner Adirondack. You’ll pass Battery Park, Ellis Island, and the Statue of Liberty as Manhattan’s lights come on. The crew, including captains such as Kat and Diana on past sailings, serves one complimentary drink and provides blankets when needed.

“Against all odds, sailing in a rain storm made it more memorable and gave us a real feel for being on a schooner. The crew was attentive and the captain experienced. Everyone came away soaked and delighted. It was a great way to celebrate my husband 75 birthday with our sons and friends.”

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NYC Statue of Liberty Tall Ship Sail aboard Clipper City - Leaving the pier beneath the Brooklyn Bridge
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NYC Statue of Liberty Tall Ship Sail aboard Clipper City

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

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

Meet at Pier 17 and sail aboard Clipper City, a large historic-style tall ship operated by Manhattan By Sail. You’ll pass the Brooklyn Bridge, Ellis Island, Governors Island, and the Statue of Liberty, with a bar and restroom onboard. This is a scenic sail, not a narrated sightseeing tour.

“Great teamwork by the crew made it a memorable trip. They worked very hard to please all customers. Highly recommended.”

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Boston: Tall Ship Harbor Sail - Raising the sails and settling into harbor time
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Boston: Tall Ship Harbor Sail

11.Tall Ship Harbor Sail

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

Step aboard a classic Liberty Fleet schooner at Fan Pier Marina for a 90-minute Boston Harbor sail. You can help raise the sails, ask the captain about landmarks, and buy Boston-brewed beer, wine, or cocktails onboard. Expect a relaxed outing with skyline views, but no formal narration and possible motor use when the wind is light.

“Lots of fun for my family celebrating my husband's 75th birthday.”

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Charleston: Schooner Sailing Harbor Tour & Dolphin Watch - Pulling away and raising the sails
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Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

12.Schooner Sailing Harbor Tour & Dolphin Watch

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

Join the captain and crew of the three-masted Schooner Pride for a 1.5-hour sail from Aquarium Wharf. You can help raise sails reaching 84 feet, drift past Fort Sumter and Castle Pinckney, and watch for dolphins. This is mainly a quiet harbor sail, not a narrated sightseeing tour, with drinks available to buy onboard.

“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 - Leaving the Historic Seaport on William Street
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Key West Sunset Sail Aboard Legendary Schooner Appledore

13.Key West Sunset Sail Aboard Legendary Schooner Appledore

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

Spend two hours aboard the Appledore, a globe-circling wooden schooner, sailing from Key West’s Historic Seaport toward Mallory Square and Sunset Key. You can help raise the sails, watch the sun fall over the Gulf, and enjoy beer, wine, champagne, cocktails, soda, and hors d’oeuvres. Arrive early for the boarding pass.

“Wonderful crew and hospitality. Appetizers were wonderful surprise and variety of drinks very good. Loved the Maine connection.”

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Portland Tall Ship Cruise on Casco Bay - Leaving Maine State Pier for Casco Bay
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Portland Tall Ship Cruise on Casco Bay

14.Portland Tall Ship Cruise on Casco Bay

★★★★★★★★★★4.5 · 235 reviews · 2 hours (approx.) · from $102

Set sail from Maine State Pier aboard Bagheera, Wendameen, or Timberwind, historic Maine-built schooners that carry up to 45 people. You can bring snacks, beer, wine, or a meal, and ask the crew about helping with the sails or taking the wheel. Expect a calm coastal outing, not a formal narrated tour.

“The “captain” shared a brief history of this lovingly restored boat before setting out for our 2 hour cruise. It was a sailing vessel, but we were motored the whole trip. 4 star rating due to overcrowded feel, lack of and water, snack etc/ even for purchase, uncomfortable seating, no shaded areas to escape. The crew was young and friendly. Woman at ticket office not so much. Didn’t feel like the thrill it could have been.”

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Schooner Clearwater- Sailing Cruise-Clearwater Beach - Why the Crew Makes a Difference
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Schooner Clearwater- Sailing Cruise-Clearwater Beach

15.Schooner Clearwater- Sailing Cruise-Clearwater Beach

★★★★★★★★★★5.0 · 229 reviews · 2 hours (approx.) · from $80

Spend two hours aboard Schooner Clearwater with Captain Tim and his crew. Motor from Clearwater Beach Municipal Marina through Clearwater Pass, then shut off the engine and sail offshore. Expect a small group, sparkling water, dolphin-spotting chances, sunset views, and a genuine sailing experience rather than a motorboat ride.

“Incredible experience, wonderful captain and crew and highly recommended! The sail boat was beautiful. We were staying at the Opal Sol and conveniently could walk to the pier. 10/10 would recommend this sunset cruise!”

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Newest in Tall Ship Sailing in the USA

★ 5.0Public Schooner Sail in GreenportFrom $1658 reviews
★ 5.0Schooner Appledore Day Sail with Full Bar in Key West89 reviews
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★ 5.0Sail on Tall Ship Windy, join us for our “Chicago Skyline Sail”From $9120 reviews
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