There is a perfect moment of sailing on every voyage. It happens just after the engine is shut off, after the sails snap at the wind on their way up the mast, after the boat falls off the wind’s nose searching for her heading.

It’s when she surges forward under her own power, slicing through the waves and sailors feel the wind rushing past their ears, hear the water rushing past her hull. It’s a physical experience that elicits an emotional response of recognition: Ahhhh, now we’re sailing; this is sailing.

Aboard the America 2.0 on a recent afternoon, the moment was marked by a collective “Ooooh” from the dozens of guests aboard the large schooner. Because make no mistake, this excursion is unlike what the other party boats in Key West have to offer. It’s not about the free beer (although there’s that, too), or about snorkeling or glib descriptions of Sunset Key. This trip is the chance to experience the primal sensation of sailing aboard a well-made craft in beautiful blue water. It’s about “burying the rail” — a sailing term that describes how the boat tips when the sails are loaded with power.

“What we do better than anybody else, hands down, is sail,” said Richard Scarano, vice president of Classic Harbor Line. “It’s fun to get out there. And for those that have never been out on a sailboat — or a big sailboat — it turns them on to something new.”

Classic Harbor Line has two boats in Key West. The America 2.0 is a brand new 100-foot-long recreation of the famous 19th century schooner that first won the America’s Cup in 1851. The Adirondack III is a 1890’s-style pilot schooner that is 80 feet long.

The America 2.0 boasts 3,500 square feet of sail area. With a light hull, carbon fiber free standing masts and a wing keel, she’s truly a nimble boat. Wide decks and outward-facing ergonomic seating around the cabin make her comfortable. The extremely able crew and captain make sailing look easy (although old salts would probably say that it is, given the exceptional design).

The Adirondack III is a little smaller, has a little less sail, but delivers just as much fun. This girl is made the old fashioned way, albeit with some modern materials, that old-time Keys wreckers would appreciate. Pilot schooners carried as many as 10 captains aboard, searching the areas near and far popular ports looking for boats that needed local knowledge of the water hazards they were approaching. Aboard the Adirondack III, which docks in Key West year round, guests arrange themselves on the cabin top for an intimate look at how sailing works.Capt. Andrew Neuhauser said he knows the Adirondack III backwards and forwards, and could probably sail her in his sleep. “The Adirondack III was my first command, so she’ll always have a special place in my heart,” he said. “She’s comfortable, but fast, and just a pleasure to sail.” Neuhauser now captains the America 2.0, aided by three mates.Captain Chris Martin and two mates are in charge of the Adirondack III. Both boats are well maintained, and both are crewed by knowledgeable and friendly locals. On a recent afternoon, Mark was cheerfully crewing, fetching icy brews and sharing his stories aboard the America 2.0. He caught the sailing bug during his final year of college acquiring an engineering degree.“This is the best job in the world,” he said, “I get to come out here and sail on this boat.” This love affair with the boats has spread to everyone connected to the operation.Sunny Andracchio, general manager of the Classic Harbor Line in Key West, readily admits that it almost killed him when the Scarano-built America 1.0 left Key West in 2005. “It broke my heart. It was like losing the best woman in the world,” Andracchio said. Andracchio makes a point of being on the dock to greet the guests disembarking from a trip. “I am there to thank them. I never ask them, ‘Did you have a good time?’” he said. “And yet they are always so happy, always say it was worth the price of the ticket and that it was the best thing they did in Key West.”

Captain Chris Martin and two mates are in charge of the Adirondack III. Both boats are well maintained, and both are crewed by knowledgeable and friendly locals. On a recent afternoon, Mark was cheerfully crewing, fetching icy brews and sharing his stories aboard the America 2.0. He caught the sailing bug during his final year of college acquiring an engineering degree.“This is the best job in the world,” he said, “I get to come out here and sail on this boat.” This love affair with the boats has spread to everyone connected to the operation.Sunny Andracchio, general manager of the Classic Harbor Line in Key West, readily admits that it almost killed him when the Scarano-built America 1.0 left Key West in 2005. “It broke my heart. It was like losing the best woman in the world,” Andracchio said. Andracchio makes a point of being on the dock to greet the guests disembarking from a trip. “I am there to thank them. I never ask them, ‘Did you have a good time?’” he said. “And yet they are always so happy, always say it was worth the price of the ticket and that it was the best thing they did in Key West.”

Sunny Andracchio, general manager of the Classic Harbor Line in Key West, readily admits that it almost killed him when the Scarano-built America 1.0 left Key West in 2005. “It broke my heart. It was like losing the best woman in the world,” Andracchio said. Andracchio makes a point of being on the dock to greet the guests disembarking from a trip. “I am there to thank them. I never ask them, ‘Did you have a good time?’” he said. “And yet they are always so happy, always say it was worth the price of the ticket and that it was the best thing they did in Key West.”

Capt. Andrew Neuhauser said he knows the Adirondack III backwards and forwards, and could probably sail her in his sleep. “The Adirondack III was my first command, so she’ll always have a special place in my heart,” he said. “She’s comfortable, but fast, and just a pleasure to sail.” Neuhauser now captains the America 2.0, aided by three mates. Captain Chris Martin and two mates are in charge of the Adirondack III. Both boats are well maintained, and both are crewed by knowledgeable and friendly locals. On a recent afternoon, Mark was cheerfully crewing, fetching icy brews and sharing his stories aboard the America 2.0. He caught the sailing bug during his final year of college acquiring an engineering degree.“This is the best job in the world,” he said, “I get to come out here and sail on this boat.” This love affair with the boats has spread to everyone connected to the operation. Sunny Andracchio, general manager of the Classic Harbor Line in Key West, readily admits that it almost killed him when the Scarano-built America 1.0 left Key West in 2005. “It broke my heart. It was like losing the best woman in the world,” Andracchio said. Andracchio makes a point of being on the dock to greet the guests disembarking from a trip. “I am there to thank them. I never ask them, ‘Did you have a good time?’” he said. “And yet they are always so happy, always say it was worth the price of the ticket and that it was the best thing they did in Key West.”

“This is the best job in the world,” he said, “I get to come out here and sail on this boat.” This love affair with the boats has spread to everyone connected to the operation. Sunny Andracchio, general manager of the Classic Harbor Line in Key West, readily admits that it almost killed him when the Scarano-built America 1.0 left Key West in 2005. “It broke my heart. It was like losing the best woman in the world,” Andracchio said. Andracchio makes a point of being on the dock to greet the guests disembarking from a trip. “I am there to thank them. I never ask them, ‘Did you have a good time?’” he said. “And yet they are always so happy, always say it was worth the price of the ticket and that it was the best thing they did in Key West.”

The boats are owned by the Scarano Boat Building company headquartered in the port of Albany, N.Y. It’s unusual for excursion boats to be owned by the builder, but the Scarano firm has made a successful foray into this branch of tourism. The Classic Harbor Line commands five ships in New York City, two boats in Key West and another in Newport, Rhode Island. The America 2.0, the flagship of the enterprise, winters in Key West and summers in New York City. She will be leaving sometime in May to head north, while the Adirondack III stays in Key West year round. All the boats have a bit of history.

“We specialize in building excursion and attraction boats that are, for the most part, period boats. Of course, the designs have been modified to achieve Coast Guard certification for passenger use,” Scarano said. The Classic Harbor Line meets every safety standard from easily accessible life jackets to a very experienced crew. About the only thing that it can’t guarantee is the wind.

“On days with a light wind, it’s a very relaxing tour of the harbor,” said Capt. Neuhauser. “But when the wind’s blowing it’s really exciting to be out there. Both novices and old sailors will have a great time.” Our advice: Pick a windy day and hang on.