The 12 Best Sailing Cruises in the USA

1.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

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

Board the 84-foot Schooner Pride at Aquarium Wharf for a 90-minute, mostly quiet sail around Charleston Harbor. The crew raises the sails by hand, points out Fort Sumter, Patriots Point, USS Yorktown, the Battery, and the Ravenel Bridge, and may let you help with the lines. Bring snacks, buy drinks on board, and watch for dolphins.

“The crew is pleasant and outgoing. It was really a nice experience especially for my wife who is not a friend of water.”

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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

Board the Liberty Star at Marina Overlook for a relaxed 90-minute sail around Boston Harbor. Captain Fredo and crew members Jess and Max may invite you to help raise the sails, while you enjoy skyline views, snacks, drinks, and fresh air. The route depends on wind and conditions, so this is a sailing experience, not a guaranteed trip to the harbor islands.

“Just loved the sailboat — not your usual tourist attraction, but definitely something worth doing! Pure zen time: peaceful, beautiful, unforgettable.”

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3.Seattle Sailing Harbor Tour

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

Spend about two hours sailing from Pier 66 Bell Harbor Marina aboard a historic tall ship. The crew may invite you to help raise the sails, while the captain shares the water with you from a comfortable, relaxed setting. Buy drinks and snacks onboard, watch for Mount Rainier and the Olympic Mountains, and return to the same downtown pier.

“We had such an amazing time. The crew was very friendly and took care of us throughout the sailing adventure. I also enjoyed the great wines being served, being able to help with the sails and of course - the views were stunning.”

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4.Tall Ship Harbor Sail

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

Leave Fan Pier Marina aboard a classic Liberty Fleet schooner and spend 90 minutes under sail in Boston Harbor. Expect skyline views, harbor traffic, open water, and a friendly crew who may let you help raise the sails. Drinks are sold onboard, but narration is informal rather than scheduled.

“This was such a fun afternoon activity! We had a long layover in Boston so wanted to get out of the airport and do something fun to kill some time. We’ve been to Boston before and done one of the other Harbor Cruises but this was even more fun! The whole crew is so personable and makes the entire ride interactive. They let anyone who wishes to help with raising and lowering the sails. They chat with everyone but also tell little stories and tell you various facts about the boat you’re on and other Boston fun facts. The whole experience was so much fun. We will definitely save this…”

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5.Schooner Sailing Harbor Tour & Dolphin Watch

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

Join the captain and crew aboard the three-masted Schooner Pride at Aquarium Wharf for a 1.5-hour Charleston Harbor sail. You can help raise sails reaching 84 feet, pass Fort Sumter and Castle Pinckney, and watch for dolphins. This is mainly a peaceful boat ride, not a fully narrated history tour. Drinks are sold on board.

“The crew was very personable and the ship was perfect. They raised sail as soon as the ship was away from the dock. Well priced and worth it.”

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6.Downtown Harbor Sailing Cruise

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

Sail Boston Harbor aboard the classic Adirondack III or IV, a pilot schooner that passes the Fish Pier, Castle Island, Moakley Courthouse, Aquarium, and Inner Harbor Islands. Captain Teresa, Captain Adam, and other crew members have earned praise for friendly service and clear answers. Choose a 90-minute or 2-hour cruise, bring a picnic, and pay onboard by credit card.

“Captain Adam took us on a great cruise around the harbor - lots of fun with an upbeat crew and wind in our sails.”

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7.Tall Sailboat Sunset Harbor Cruise

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

Spend two hours aboard the schooner Bay Lady, sailing from Pier 66 as the sun drops behind the Olympic Mountains. You can help raise the sails, take a turn at the wheel, and buy beer, wine, cider, champagne, snacks, or soft drinks. Bring warm layers: the boat sails rain or shine, and the evening breeze can feel cold.

“Best experience we have had here. The captain and crew were tremendous.”

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8.Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

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

Spend about two hours sailing from Boothbay Harbor’s historic waterfront aboard the schooner Eastwind. You may help raise the sails, watch for seals and porpoises, and take in islands, lighthouses, and ocean views. Captains and mates such as Sarah, Josh, Luke, Christine, and Mareson are known for friendly, hands-on service. Bring non-alcoholic drinks and snacks, or buy beer, wine, and liquor on board.

“Amazing. Fun. Beautiful views. Great captain and mate. Such a good time with interactive hoisting the sails.”

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9.Sunset Tall Ship Harbor Cruise

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

Spend two hours aboard Liberty Fleet’s classic tall ship, sailing from Fan Pier Marina around Boston Harbor at sunset. You can help hoist the sails, ask the English-speaking crew about landmarks, and possibly take the wheel. Drinks, including Boston-brewed beer, are sold onboard, but food is not included.

“We enjoyed this excursion so much. The crew was absolutely phenomenal. Professional while also being really fun, funny, and entertaining. They're characters for sure in the best way. We loved our time on the ship!”

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10.Tall Ship Harbor Cruise

★★★★★★★★★★4.7 · 86 reviews · from $73

Board the schooner Bay Lady at Pier 66 for a two-hour English-language harbor sail. Crew members Anthony, Madison, and Clark may invite you to raise the sails, steer, or watch a small cannon fire. Expect Seattle skyline views, possible Mount Rainier sightings, marine life, drinks for purchase, and a rain-or-shine outing.

“Loved the cruise I just wish there was more narrated information”

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11.Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) Top rated

Spend two to four hours aboard Fate, a private 50-foot sailing yacht for up to six people. Captain Scott, Will, Adam, and first mates Sam or Monique may guide your cruise past the Battery, Ravenel Bridge, USS Yorktown, and possibly Fort Sumter. Soft drinks and water are included, and you can bring your own alcohol.

“The Sailboat is absolutely beautiful and perfect for a sail around the harbor. Captain Will & First mate Sam were great hosts and super knowledgeable! They made the trip that much more enjoyable... Highly recommend...”

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12.Schooner Applejack Sunset Sail Tour in Boothbay Harbor

★★★★★★★★★★5.0 · 42 reviews · 2 hours (approx.) · from $59

Spend about two hours aboard Schooner Applejack with Boothbay Sailing, leaving from 15 Wharf Street in Boothbay Harbor. Captains and mates such as Luke, Kate, Christina, Brian, Sean, and Shawn share local knowledge, help you raise the sails, and point out seals or porpoises when the harbor wildlife appears. Bring a light jacket and your own nonalcoholic snacks.

“We took the sunset cruise. The weather was awesome and the crew, Luke, was amazing. A must do when in Boothbay Harbor!”

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