Howdy Bailey is responsible for building some of the finest yachts to ever come out of Hampton Roads.
by Lorraine Eaton
On a summer morning in 1973, well before sunrise, Howdy Bailey stood at the top of the Henry H. Buckman Bridge in Jacksonville, Florida, a block-and-tackle and a coil of rope slung over one shoulder. He tied the rope to the rail, dropped the pulleys over the side and lowered them until they swayed dangerously just above the surface of the St. Johns River, 65 feet below. Then he got into his car and drove away.
He returned a few hours later, this time by sea, captaining a 45-foot ferrocement sailboat he built himself. Bobbing horizontally behind the boat on two inner tubes was the 62-foot mast, the pole designed to support the boat’s largest sail.
To finish the boat, Bailey need to attach the mast to the deck. He had no money to hire a crane, so Bailey decided to use the bridge. That morning, Bailey and some friends eased his boat under the bridge where the block-and-tackle dangled. They cut the engine and tied the sailboat between the bridge stanchions. Then they secured the top of the mast to the block-and-tackle and began slowly raising it.
They just about had the mast in the right spot when police showed up. The officers yelled down to Bailey, informing him that he was breaking the law. Attaching anything to a public bridge is illegal and dangerous, they said. But Bailey had gone too far to stop.
“If you want to cut the rope, you can, but you might kill some of us,” he yelled back up to them. “It was early in the morning, so they were still in a good mood, so they said, ‘Well, why don’t you go ahead and finish the job. We’ll just kind of forget we’ve seen you.’ We never pulled a stunt like that again.”
That is a story of Bailey’s first yacht. Before retiring from yacht building in 2000, Bailey, 81, built 30 vessels – from barges to million-dollar yachts – and along the way earn the reputation as the Chesapeake Bay’s preeminent custom metal-boat builder.
Photos tile the office walls of Howdy Bailey Yacht Services in Norfolk. The sloops, barges, cutters and cruisers – some under full sail, others “on the hard” in boatyards – are interspersed with framed magazine articles about his boats, and plaques thanking Bailey for his charitable work.
“I’m more than lucky,” Bailey said, looking around the room at his life’s work, his trademark floral ballcap sitting square on his head. “I’m living the dream that I dreamed.”
The ferrocement boat, eventually christened “Dylan” after his son, may have been the first yacht that Bailey built, but it wasn’t his first boat. That honor goes to a dugout canoe he made with friends in Panama. Bailey, a New Orleans native, moved there at 10 when his dad began work on the Panama Canal.
After high school, Bailey joined the Navy. His first posting: Cuba. Next came a stint aboard the Norfolk-based USS Saratoga, where he specialized in catapults and arresting gear. He saw Europe and acquired some discipline and management skills. But after leaving the Navy, he thought, Catapults and arresting gear; what do you use that for?
As it happened, that experience, combined with an apprenticeship in Florida that trained him in steam fitting, welding, plumbing and air conditioning, prepared Bailey for the rigors of owning and building boats.
His first attempt was decidedly unsexy. In 1972, after his apprenticeship, Bailey ran a fabrication shop in Jacksonville where he finished Tortuga, a 60-foot steel utility barge meant to haul water and fuel.
He launched Dylan the following year. It was a smart first step. Ferrocement sailboats, made of welded steel ribs covered in cement plaster, are considered the easiest and cheapest boat for amateurs to build.
Then in 1974, with $600 in his pocket, Bailey quit work and charted a course to Rhode Island and the America’s Cup yacht race. Neither he nor his sole crewmember had sailed at night, or in the ocean, for that matter. The sailing manual they packed was no help. It took 15 days to make Annapolis, a trip that would take a moderately skilled sailor just five or six.
“Clueless,” Bailey said. “Absolutely clueless.”
They never made it to the America’s Cup. Instead, Bailey began living a life of intermittent retirement, living aboard Dylan in Annapolis and working union jobs just long enough to support his boat habit. He would then sail off to Bermuda, Florida or the Caribbean when he had enough money.
For eight years, he and wife Joanie, a flight attendant, made 24 offshore crossings aboard Dylan, logging 52,000 ocean miles. He gained a reputation as an expert sailor and began helping yacht owners by moving and crewing their million-dollar boats. Before long, he dusted off his welding tools, pulled down his face shield and began building them, too.
Probably one of his proudest accomplishments was when he built Rising Sun, a 64-foot staysail schooner conceived by South African boat designer Dudley Dix. Bailey had
already built the iconic Norfolk Rebel, a sail-powered tug for the late, legendary Capt. Lane Briggs, a boat that still draws stares at a Willoughby Spit marina. Then came the
Eagle, a 75-foot, three-masted schooner and another, smaller steel sloop.
At the time, the yacht-building tide was turning from composites such as fiberglass toward steel and aluminum. Under construction, the metal hulls looked like gleaming tunnels. Once finished, they looked identical to fiberglass.
Bailey had already made a name for himself, launching a series of boats at the Little Creek boatyard that turned heads. But it was Rising Sun that made him a star. The yacht debuted in 1986 at the Annapolis Boat Show, a premier East Coast showcase for the latest models.
Attendees who made it onboard found a wonderland of stained glass, gleaming teak, a plush banquette, a library, three staterooms and separate crew quarters forward. And with 2,200 square feet of sail on deck, there was “enough room to throw a barn dance,” gushed the review in The Illustrated magazine. “Right away you know you are on a special kind of yacht.”
The price: $1.3 million in today’s money.
A tide of commissions rolled in. Six boats in 1988 including the 67-foot schooner Virginia Rover, then three in 1989, including a steel push tug, a cutter and a fantail cruiser, and three more in 1990. That year he bought a slice of land at Little Creek, opened his own facility and built a towering shed so that he could build aluminum boats indoors and steel outside.
Commissions kept coming: the Patriot, a 65-foot steel passenger ferry that still plies between St. Michaels and Baltimore; Thumper, a 67-foot aluminum ketch; and Oceanstar, an 88-foot steel schooner for Ocean Navigator magazine. Refits included Geraldo Rivera’s
68-foot ketch, Voyager, which the celebrity then sailed around the world.
“I designed a bunch of steel and aluminum sailboats for him and his customers, as well as one powerboat,” said Dix, the award-winning designer who now lives in Virginia Beach. “Howdy built all of them to a very high standard of construction and finish, all boats of which we both felt very proud.”
One of Bailey’s most high-profile builds – and most controversial – was Imagine, a feather-light, 60-foot recycled aluminum yacht with a 100-foot mast and a 15-foot keel that was capable of slicing through seas at 30 knots – Ferrari-fast for a sailboat.
Imagine was built for the BOC Challenge, a solo around-the-world race. Locally it garnered a bit of civic pride, with the city of Norfolk providing the $7,500 entrance fee. But the boat was damaged during its first sea trial in 1993. Talk of lawsuits followed and plenty of press named Bailey as the builder.
He was not implicated, but there have been lawsuits. Bailey once declared bankruptcy. But three years later, he was whole again and back building metal boats in his own facility. His last boat, the three-masted, 49-passenger schooner Liberte, designed by Dix and splashed in 2001, still charters in Cape Cod and Annapolis.
Along the way, Bailey raised thousands of dollars for local charities. He designed and donates trophy belt buckles for sailing regattas, and he built two chairs designed to allow disabled people to sail to the Hampton Roads community sailing center.
These days, Bailey and longtime employee Larry Foster still work the boat trade, creating elegant teak interiors and trim and custom metal everything, including a shark cage for an Jacque Cousteau Society expedition of the Antarctic and a fountain made of steel cubes destined for a client’s yard.
One of his favorite recent projects: a stainless-steel water-cooled exhaust system, hardly what the layman thinks about when imagining a $6 million yacht. Bailey, the master of metal, endures.
“It was very exotic,” he said, nonchalantly. “Actually, a work of art.”
