As Magic Carpet neared Cape Pogue, a thick fog crossed over the bow. All of a sudden, the boat was in the center of a circle of mist, though somehow the sun made brilliant that oceanic cloud.

Deftly handling the vessel on its first sail of the season were husband and wife Todd Bassett and Lee Taylor, who work as the captain, crew and co-owners of the Magic Carpet. Ever-unassuming, they run their ship, alternately perching near the helm, cranking the jib with the “coffee grinder” at the stern, or scrambling around the bow, quietly and calmly employing the instruments of their trade.

Mr. Bassett, a lifelong resident of Martha’s Vineyard, leaned against the stays of the mast, his baseball cap and blue shorts, faded by sun and time, providing the perfect uniform for a man always at sea.

Throughout the two-hour cruise in and out of Edgartown harbor, Mr. Bassett peppered the conversation with his answers to the guests’ questions about the precise location of various kinds of fish, shellfish, sharks and whales around the Island. He also spoke about the various maintenance and general upkeep required for a boat like the Magic Carpet, built entirely from wood in 1959. Thanks to stints in both swordfishing and contracting, Mr. Bassett is well outfitted in both areas of expertise.

And while Magic Carpet has been steadily showing visitors a taste of the high seas in the old-fashioned way for 18 years, the business around them — charter sailing — has changed.

“We see certainly fewer charter boats than there used to be,” Ms. Taylor said.

Much of this can be chalked up to insurance regulations, which are especially stringent for inspected vessels, which can take out up to 49 passengers, depending on capacity. Tom Grewe, the owner of the Ayuthia, who used to run charter sails out of Vineyard Haven harbor, left the business several years ago, when the cost of insurance got too high.

“A lot of people that work on the Island are maybe not 100 per cent legal, or maybe they skipped to save on a permit for this or a permit for that, but it was too expensive for us to do it legally,” Mr. Grewe said.

Some of that, according to Ms. Taylor, came after Sept. 11, when the U.S. Coast Guard moved into the jurisdiction of the newly created Department of Homeland Security.

The skyrocketing cost of insurance coupled with a depressed economy leave both boat-owners and customers at a loss for funds. While the high overhead caused Mr. Grewe formally to leave the business, the absence of a thriving market was the main problem: “People started telling me that they don’t have the cash in their pockets to spring for a sail with me. They’re spending huge amounts of money in the grocery store, huge amounts on their rent, and a huge amount to get here. Before the crunch, people could spend that way, but now they can’t.”

Capt. Hugh Taylor, who owned the catamaran Arabella until two years ago, felt similarly about the effects of the economy. “It became more and more apparent that I wasn’t bringing in the funds to be able to take care of the vessel as the economy made traffic a little less abundant.” He sold his vessel, which was the only charter running out of Menemsha harbor, in 2009.

“I miss the boat terribly and I wish I hadn’t sold it,” Mr. Taylor said, “but it’s remarkable how many people are still calling, because we’re still listed throughout the Internet, and I miss not offering a boat out of Menemsha.

“But we’re thrilled to be able to take those calls and turn that business over to Todd [Bassett] and Morgan [Douglas, of the Black Dog Tall Ships].”

For some boats, those that offer a slightly different product, the business is still there. For instance, Mad Max Sailing Adventures, which has its own dock with marina services, as well as a catamaran that can host up to 49 guests, offers a different experience.

Rather, Mad Max provides an experience for even the most casual of sailors. Said one of the boat’s captains, Mark Lacourse, “Mad Max was built for its purpose. It was built to be a day-sailer, a booze cruiser. We’re designed for what we do. We try to offer an experience — in its name, it’s a sailing adventure. We always explain when people call up that the goal is to sail as far and as fast as we can in the time provided.”

Additionally, much of their business stems from the ability to keep people comfortable, assuring them of their safety. “Our clients get the sailing experience with the comfort of being on a more stable boat, like our catamaran,” said Mr. Lacourse. “On Magic Carpet, if they go out when it’s windy, they keel way over, and when they tack, everyone has to shift and they have stuff all over the deck. They’re very talented at what they do and they have a beautiful boat, but it’s a different experience.”

Many of the clients who would go out on a charter sailing are not sailors themselves, which in part dictates the options available on the Island. People who truly appreciate wooden boats, like the Ayuthia or Magic Carpet, are unlikely to overlap with the customers who seek out the experience Mad Max offers. The breakdown is fairly simple: One is traditional, the other commercial.

But there is a slight overlap which comes in the form of the Black Dog Tall Ships, the Alabama and the Shenandoah. The Alabama, built in 1926, served as a schooner for the Alabama Bar Pilots, until her retirement in 1966, when she was bought by Robert S. Douglas, who started the Black Dog. The Shenandoah is a recreation of a traditional mid-19th century warship, a fantasy made reality by Mr. Douglas in 1964.

These ships also serve as charter boats of sorts: The Alabama functions like many of the other charters, offering public, private and overnight sails; the Shenandoah plays host to a kids’ camp for most of the summer, taking school groups from on-Island and off, as well as children from all over out for five days. At the camp, which welcomes all levels of sailing ability, the children act the part of sailors from days gone by.

While the Black Dog Tall Ships might be part of a larger corporation with significant name and logo recognition, the captain of the Alabama, Morgan Douglas, the eldest son of Robert Douglas, maintains that the family has a love for their ships, and a deep appreciation for this line of their business: “What we do is very unique. It’s a dying breed of ships, and we are committed to maintaining two of the better examples of them around.”

For Morgan Douglas and the others, at the end of the day, it comes back to the ships themselves. Said Ms. Taylor, “Any wooden boat owner is a dreamer, and it was a dream to get this boat.”

And for Mr. Grewe, though he might not be in the business of chartering anymore, his life centers on Ayuthia: “I knew within the first two weeks that I owned her that she was a special boat with a soul. She speaks to me and she has for a long time.”

Regardless of which boats sail these waters, whether made of weathered wood or gleaming fiberglass, there will always be those who care for these vessels, looking to share their love of ship and sea with those eager to venture forth into the wild blue yonder.