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A captain straight from Central Casting

Local sailors like me have their own way of dealing with Chesapeake Bay and staying fit and active. The toy I use as an older single-hander on this large inland sea of a playground is my 1962 Sailmaster 22C. I make whatever changes I feel are necessary while paying attention to safety and the wind and weather in general. Maintaining this fiberglass boat - for the last 27 years - also keeps me busy in the offseason.

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When and if the time does come for me to stop solo sailing, I have the option to continue playing on the water by going over to the "dark side." My preference would be a small, traditional powerboat - less work, more speed, space, protection and a comfortable bunk and more efficient galley.

Sailing out of my home port of Annapolis for 40 years brings me into contact with boaters who help me refine my own developing ideas to make sailing easier. With that in mind, it was a pleasure to run into Capt. William Horatio "Harry" Privette, 73, a well-seasoned offshore skipper of large, privately owned yachts.

He always seemed to be leaving for or returning from some faraway place. Lately he has been temporarily grounded in Annapolis because of limited big-boat command positions in an uncertain economy and is taking on a new seasonal job as a "diagnostician" at nearby Homestead Gardens. (Horticulture has long been his avocation.)

Privette and his wife, Grace, 51, are tying up some loose ends in town but are ready to go to sea on a delivery or get a command and a first-mate position, preferably on a fast sailing yacht in the 50-foot range bound for warm seas and romantic ports of call. "We are a team and have double-handed vessels in the plus-60-foot range," he says.

It has been three years since they left their all-time-favorite command aboard French Kiss, a Farr-designed Beneteau sloop they sailed to a third-in-class finish in the 2007 TransPac. Privette joined the 50-footer in 2002 when she was commissioned out of the box in Annapolis.

Harry and Grace met in 2005 when he was looking for crew to transit the Panama Canal to the Pacific and beyond. Grace had been a freelance canal guide and line handler there and had assisted in 40 transits. At the time, she was with her husband in the 40-foot catamaran they had built in Canada. The dashing Capt. Harry signed her on to help deliver French Kiss to Costa Rica, en route to the vessel's home port in San Francisco. She decided to stay on board, and they married in 2008 in Annapolis.

Capt. Harry and Grace, a team on and off the water, are awaiting their next adventure.

A captain right out of Hollywood's Central Casting, he longs for "more sailing of Mother Oceans and her sibling seas," he says. He looks the well-salted part, presenting a worldly demeanor and poise topped off by white hair and a white handlebar sergeant-major moustache. Standing almost 6 feet tall, he is obviously a yachtie and not a boatyard denizen, although he knows his way around aloft, in galleys and in engine rooms. His onstage wit is always on call at social interludes in the cockpit, where he trades in sea tales that include the obligatory shipwreck in a wide-ranging repertoire.

"People often ask if I have sailed all my life," he says. "I answer, not yet."

Because of his seagoing background, one can easily imagine his emotions as he waves farewell to friends sailing away on deliveries while he stays behind on the hard - temporarily, he hopes. He would dearly love to add more sea miles to a long résumé that already includes one circumnavigation, two Panama Canal transits, three Atlantic crossings, one TransPac Race and seven Southern Ocean Racing Circuits.

Born in Orlando, Fla., Privette was packed off to a Tennessee boarding school run by the Church of England's monastic Order of the Holy Cross. From there, he did a stint in the Navy (he's a retired reserve officer), which eventually led to college and gave way to a yachting career.

He crewed aboard SORC and International Offshore Rule yachts, such as Windward Passage and Condor of Bermuda. He also was a stockbroker for 18 years, an adjunct professor, a "protocol aide" to a Florida governor and an instructor in navigation and offshore racing. He also lived aboard his 54-foot Alden yawl for two years in France.

In 1984, he moved to Annapolis, where he got his 50-ton and 100-ton captain's licenses, delivered yachts and managed operations at a local charter company. There also were many big-boat races and deliveries throughout the Med-iterranean and Caribbean, the South Pacific, the Gulf and Pacific coasts of Mexico, the Eastern Seaboard, the California coast, South Africa, Cuba, Hawaii, Australia, New Zealand, Tahiti, Easter Island and the Galapagos.

To compete in the 2007 TransPac, Privette trained the owner of French Kiss and his three friends for two-and-a-half months in San Francisco Bay. "They had never sailed out of sight of land before or even spent a night aboard," he says. "They were good enough, however, to get us to Hawaii, where the owner seemed to lose interest in the boat after his father's death. He hired a delivery crew to sail her back to California, and Grace and I decided to remain in Hawaii. I had become very close to that family. They were like the family I never had."

Privette has continued to deliver yachts and sail in big-boat races, but last year he decided to tie up in Annapolis while the economy improves and to tie up some loose ends. "When we do get a new command, we would like to return to the Caribbean ... and warm weather!"

Jack Sherwood is writer at large for Soundings

This article originally appeared in the April 2011 issue.