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Real life, not work: sailing Guildive

There are two deeply evocative moments aboard the classic William Hand-designed motorsailer Guildive. One involves squatting down on the cabin sole to get an up-close-and-personal look at the original teak planks, redolent of sea salt, buffed by time — every scratch, pock and depression reflecting the wake of the ship’s nearly 80 years on the sea.

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The other occurs after you’ve motored away from the dock in Castine, Maine, where Guildive operates. Capt. Kate Kana is at the wheel, holding her 18-month-old toddler Coe. Her husband, Capt. Zander Parker, is on deck, raising the main and jib. Passengers chat in the cockpit above the sound of the engine, looking at landmarks on the waterfront — Maine Maritime Academy’s docks and brick buildings and boats, the adorable little red-roofed Our Lady of Holy Hope Roman Catholic church, the seawall protecting an important early Native American shell midden, the Georgian and Federalist homes perfectly restored and maintained by summer and year-round residents.

And then it happens. Kana shuts off the engine, there’s a slight flap in 1,600 square feet of sail as they take in the wind, and a hypnotic quiet fills the air. Conversation shuts down as eyes and ears open to the natural elements — the lapping waves, the cry of gulls, the feel of a wooden vessel sluicing through the sea.

For Parker and Kana, and now their young ambassador Coe, offering this grande dame as a tour-boat adventure amid Castine’s beautiful environs is a dream come true. They love the melding of history their operation offers — the various stories behind William Hand, the Guildive and Castine; the fact that another Hand icon, the famed Arctic schooner Bowdoin, is docked nearby at Maine Maritime; even their own sagas of sailing the deep blue on all manner of ships.

And they love the act of sharing. It has turned a ton of customers into friends. On this trip, folks enjoy the view from the comfortable vantage of a sheltered cockpit as Kana and Parker take turns pointing out sites and seals and explaining the area’s role during the War of 1812, when locals set up a blockade against the British. Soon everyone is breaking out sandwiches from their packs — lobster rolls figure large — and Parker takes a turn at the helm while Kana, tightly holding the strap of Coe’s life vest, good-naturedly allows the youngster to play a game of pushing fenders off the side decks.

“We’ve been having a blast,” Kana says once Guildive has returned to the dock.

Kana and Parker are the picture of vigor, both expert multitaskers who handle the helm, chat with passengers, maintain a sharp eye in all directions and manage their energetic toddler — who has inherited his mother’s Nordic beauty — all at once. They trade off duties with barely discernible communications. One moment, Kana’s at the helm, the next, Parker.

“We thought we’d get people who have sailed before, but it’s amazed us,” says Kana. “We get lot of people who’ve never been on a boat, both kids and adults. To be able to share this experience with them, in this setting, has transformed us, and it’s transformed them.”


The Hand motorsailer is a special kind of boat that speaks of the incursion of the newfangled engine into the age of sail. Hand began designing motorsailers in the late 1920s after several decades of work that had already made him one of the 20th century’s most prolific naval architects. Born in 1875, Hand worked in New Bedford, then Fairhaven, Massachusetts, designing motoryachts, record-breaking speedboats, fishing launches, tunnel-drives, schooners, patrol boats, rumrunners and cruising sailboats of every description.

“But all of this was a prelude to the 14-year period (1926-1940) in which he would create the unique Hand motorsailer, making his mark as firmly as with any sculptor’s chisel,” Jerry Kirschenbaum writes in WoodenBoat magazine’s May/June 1979 issue. “Hand did not design boats. They evolved. Each boat was a laboratory, distilling past experiences and simultaneously carrying the genes of designs to come.”

Kate Kana and Zander Parker hold Coe, their new deckhand.

Hand was influenced, on the one hand, by the sloops in Maine, where he was born, and by the sharpies and bugeyes on Chesapeake Bay, where he spent time as a child, thanks to his father’s career with the Revenue Cutter Service — the forerunner of the Coast Guard. On the other hand, the internal combustion engine had found its way into boats. “The engines were there, the fuel was there, but the hulls were a legacy from another century, sailing models that wouldn’t respond to high power,” writes Kirschenbaum.

Hand took this as a challenge to design vessels that do well under both sail and power. Not merely “sailboats with overgrown auxiliary engines,” Kirschenbaum continues, Hand’s designs reversed the hierarchy, with an engine for main power and sails as auxiliary. He started with the proven reliability and seaworthiness of the New England dragger, fined up the forward sections, improved the entry, lightened the displacement and improved sailing performance. His motorsailers were soon widely known as beautiful, reliable and comfortable at sea.

Hand was hired by the Wheeler shipyard in Brooklyn, New York, to design motorsailers for its production line. The Great Depression was rolling in, but the yard must have figured it would be profitable to leverage Hand’s star power in the yachting world. A Wheeler ad called Hand the “outstanding authority on the design and construction of boats for open ocean use.” And continued: “The general design of these boats incorporates the splendid sailing features of the offshore fisherman models combined with the lines of a good offshore power cruiser resulting in a boat which is splendid under power and moderately fast under sail.”

Guildive, originally named Restless, was built as a private yacht for Stuyvesant Fish II, a sportsman and prominent scion of a Gilded Age family, and launched in 1934. At 56 feet, it was the largest of the series and the only one of its size; others were in the 30- to 40-foot range.

Upon its launch, the earliest yachting magazines, Rudder and Motor Boating, noted Restless’ grace and seaworthiness. In 1942, like countless other yachts and fishing vessels, Restless was requisitioned by the Coast Guard for coastal patrol, off New Jersey and Long Island, during World War II. After the war, the boat went through several owners and name changes, sailing the waters from Canada to the Caribbean many times. One of those owners was John Mason, of St. John, U.S. Virgin Islands, who ran charters in the Caribbean in the 1960s. The boat held up well over the years, but upkeep is the name of the game with any wooden boat. In 1981, Mason was preparing to sell the motorsailer to Richard “Dmitri” Bernhardt of Bailey Island, Maine, and in a letter to him pitched the boat’s condition as a plus: “After all, if you want a 47-year-old boat or have had any experience with one, there is usually a little rot here and there now and then. It gives you something to do in your off time.”

Bernhardt and his wife renamed the boat Sixpence and raised their daughter on board, sailing between Canada and the Caribbean. They performed a long-term restoration in the 1980s, then home-ported the boat on Orr’s Island in the 1990s and ran overnight charter cruises in Casco Bay. After 30 years or so, Bernhardt decided to sell the boat but was particular about choosing new owners.


Enter Kana and Parker, both of whom have tremendous maritime experience. They are Coast Guard-licensed and have sailed a combined distance of more than 40,000 nautical miles on the North Atlantic, South Pacific, California coast, Great Lakes and the West Indies to Iceland.

Raised on Maryland’s Eastern Shore, Kana grew up sailing small boats and racing in high school and college, winning national collegiate championships. She never conceived of sailing as a paying job; at college, she studied the classics. Partway through, “I thought, the classics have been there for 2,000 years. They’ll still be there when I get out of college,” she recalls. She found the Sea Education Association’s Semester at Sea program and sailed between Hawaii and Tahiti.

Guildive is traditional, with a few modern touches for comfort’s sake.

It was a revelation to realize the instructors were paid to be on the water. “I said, ‘Wow! I want to do that!’ ”

Back at college, she continued to sail during the summer, working her way from deckhand to chief mate, aboard the schooners Harvey Gamage and Lady Maryland, both offering educational programs to youth. After college, she headed west to the Los Angeles Maritime Institute, a youth-empowering program aboard the tall ships Irving Johnson and Exy Johnson.

Parker grew up in Antigonish, Nova Scotia, spending weekends sailing a Laser. Around 2000, he had finished college and signed on to the barque Picton Castle, a square-rigger home-ported in Lunenburg, Nova Scotia, offering offshore training for adults. He loved it, so he enrolled at Maine Maritime, attracted by the opportunity to work on the Bowdoin. Parker earned a degree in small vessel operations and his mariner’s license — and landed at the Los Angeles Maritime Institute, where he met Kana.

They both loved the work but yearned for the East Coast. It was difficult to find a ship that they could work aboard together while allowing each to advance their individual skills. So Parker shipped out on the Bluenose II in Nova Scotia, and Kana worked on youth-education vessels in the Chesapeake.

A few years of separation was a bit much. They found a unique venture in Hawaii, where a new outfit called Island Ventures offered packet service aboard an old fishing trawler converted to sail, named Kwai, to the remote Cook Islands, where cargo service was infrequent. Parker signed on as mate, Kana as purser.

“Beyond the fact that, holy moley, you get this opportunity to go to a place hardly anyone gets to visit, but it was also in a unique package,” Kana says. “We’d bring flour, rice, sugar, cement, ramen noodles, building equipment, flip-flops, coolers, ketchup, frozen chicken. All stacked in, everything you could imagine for six months because that’s how long it would be before the islands would see the boat again.”

Hopping between tiny islands, the crew delicately navigated community relations. If two villages were feuding, heaven forbid if their cargo was touching. Kana sometimes had to track down payments, or the boat wouldn’t have money to refuel; she’d find herself carrying around tens of thousands of dollars in a backpack. Crewmembers had cargo shares, so it was everyone’s duty to make sure not a drop of water hit it.

“If you kept the cargo dry, you got paid,” Kana says. “So Zander and I went from taking kids sailing to keeping palettes of cement dry. You’re covered in grease, and you haven’t showered in days, and you’re tired, and you’re worried about cement. But we got to see these places in the world that are hard to get to.”

The couple would have continued on the Kwai, but a new adventure came along.


It was the winter of 2008. They were looking for their “dream boat” for charter tours and educational programs. Sixpence was listed online by an Annapolis, Maryland, broker — “kind of” in their price range. They went to visit. “Sure enough, you walk on board, and it’s spectacular,” Kana says. “You can visualize people being on board and comfortable in Maine weather. We knew we’d start the business in Maine, and we knew we wanted a big boat for a few people.”

Bernhardt was particular about whom he would sell Sixpence to. “It was like an interview,” Kana recalls of the initial meeting. “He wanted to know if we were capable of handling a boat like this. He said, ‘You can ding up the paint and scratch the varnish. It doesn’t matter what shoes you wear on the boat. All of that can be fixed. But it can’t just sit there at the end of a dock and be a trophy.’

“We said, ‘That’s perfect because we’re going to bring a lot of people on board, and we don’t know what shoes they’ll be wearing. We’ll have people who’ve never sailed before. We want them to be comfortable.’ ”

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The deal was settled, and the couple launched their business the following summer. Castine was perfect. No other boats offered sail charters to accommodate the area’s small but stable tourist and summer resident population, and MMA’s summer programs generate passengers. The town is a historic attraction, and the harbor offers wonderful sightseeing. Year-round families also enjoy being on the boat, especially when guests are in town.

Neither of the previous names, Restless nor Sixpence, spoke to the couple. They liked Guildive, which they pronounce as an Anglicized “gill-dive” — Old French for “rum.”

“It was part of our intention to voyage with her back to the Caribbean, so doing the rum history and rum island tours would keep the spirit of Guildive alive,” explains Parker.

Initially, they operated during summers in Castine and winters in the Chesapeake. Sailing between locales twice a year, they invited customers to go along as crew.

“Our style was pretty fluid,” says Kana. “We’d ask them to participate as much as they felt comfortable, anything from chopping veggies to standing watch in the middle of the night. Of course, one of us was always awake. It was a neat dynamic. Everyone became one unit instead of five strangers.”

Now the family stays year-round in Castine. At times, the couple misses sailing offshore. “But we also know how incredibly lucky we are to have found a great boat and a great location,” Kana says. “And we’ve come away with so many friends. Just the other day, we got a thank-you note in the mail from someone who sailed with us early on. It makes us feel like this is real life, not work.”

This article originally appeared in the September 2016 issue.