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The 90-year-old tech wizard

Maxwell Simkin’s passion for boating blazes as strong today as it did 75 years ago, when a high-school teacher who saw all kinds of potential in this kid from the Bronx kindled the fire and taught him to sail.

Maxwell Simkin’s passion for boating blazes as strong today as it did 75 years ago, when a high-school teacher who saw all kinds of potential in this kid from the Bronx kindled the fire and taught him to sail.

Start them early, and they're more likely to become lifelong boaters. Here's a loook at some remarkable young and not-so-young sailors. Read the other stories in this package: From Cradle to Grave   The 71-year-old Blue Water Medalist   The 84-year-old with a new motorsailer   The 89-year-old designer

At 90 Simkin still sails, and he still is learning. He has made the annual fall pilgrimage from his home on Long Island, N.Y., to Florida 51 times. He usually sails much of the way offshore; sometimes he goes it alone.

Tapping at the keyboard of his computer, the widower from Greenport stays busy while living alone aboard his sailboat in Florida during winter. He keeps a daily routine aboard Sea Fever, his Scheel 45. He rises early and downloads and analyzes wind gradient files from NOAA to keep abreast of the weather. He’s a stock market whiz, and he buys and sells over the Internet. Before making a trade, he consults software that both downloads transactions daily for every stock on the exchange and analyzes 15 years of market data.

Simkin also is a ham radio operator and checks in on the Waterway Net at 7:45 a.m. to hear reports from cruisers on matters ranging from broken drawbridges to hurricane holes to overdue boats. He keeps in touch with friends, regularly e-mailing them or reaching them by voice on Skype, a way of phoning free on the Web using his computer.

The retired oral surgeon swims easily through the flood of new technology; he enjoys the challenge. When he’s at sea he can use his computer, a special modem and software called Airmail to make calls over his ham radio and connect his computer to the Internet. He does it through land-based ham operators who have linked their radios to their computers through a software program called Winlink.

“I send and receive e-mails [over the radio]. I receive weather products. It’s just marvelous,” he says. “It’s a lot different than the old days.”

Simkin has a suite of navigation electronics as well as an autopilot and a large library of paper charts stowed away in a case he designed himself. The electronic conveniences give him a bigger margin of safety on the water, but they also “keep my brain working,” he says. “If you want to have fun in life, you have to try to keep up as much as you can with the modern world.” That’s one of his secrets to growing old gracefully.

Simkin has an artist’s hands. Before he retired 28 years ago from his practice, he used those hands to reconstruct damaged mouths, becoming one of the top practitioners in his field. Today, he occupies himself sketching portraits in pencil or pursuing a new discipline, painting. He has completed a near-perfect likeness in pencil of Winston Churchill. His work in progress is a watercolor of his late wife, Muriel, a partner in life and sailing until her death 16 years ago in an auto accident that still weighs heavily on Simkin. Though it wasn’t his fault, he was at the wheel when another car broadsided theirs.

Muriel was smart, sociable, always smiling — and she loved to sail. “She was such a great partner. I never tried to pick up with anyone else,” he says. “To me, the most important thing in life is the person you marry. What else is important? Boats? They don’t mean much.”

Yet sailing remains a huge part of his life. “It keeps me going,” he says. “I poke around. I meet new people wherever I go.” On Sea Fever he navigates a network of relationships based on a common interest in sailing and cruising. He is a member of the Cruising Club of America and the Waterway Radio & Cruising Club, and is active in the Fort Lauderdale-based Seven Seas Cruising Association. He attends their meetings and social events when he can, and cruises from time to time with people he knows through these groups.

“I live on my boat six months out of the year,” he says. That is where he always wanted to be, why as a struggling young dentist with a wife and 6-year-old child he built his own L. Francis Herreshoff-designed ketch. “I was trying to fulfill my dream,” he says. He has loved boats and the water since high school, when he spent tips from his drug store job to rent a rowboat for fishing.

“It was always a challenge,” he says. And Maxwell Simkin was always up for a challenge. “It was freedom, the freedom of the open air. It was the luxury of being able to go wherever in the world you wanted to go. The world was your oyster. It was the beauty of the sea. It was the pleasure of arriving somewhere, your destination, and knowing that you planned it all and navigated there. It was all the people you met along the way.” And for many years, it was about doing all this with the woman he loved. Muriel is gone now, but Simkin still is sailing.

He celebrated his 90th birthday Nov. 14 at the Loggerhead Marina in North Palm Beach, his home this winter. By March he planned to be sailing back north to his house on Gull Pond on Long Island’s north fork.

“I go to the Bahamas almost every single year,” says Simkin, or “Mac,” as he asks to be called. He may sail with crew or voyage alone. He has cruised the Bahamas every year for the last 16 and most years for the past 35. He waits until March, when the winter winds mellow and the Florida Straits settle down. He pokes around the Abacos, which he knows well, and anchors out so he doesn’t have to thread his way through shoal water to get into the marinas. “It’s hard for one person to run a big boat,” he says. “I kind of play it safe.”

Snowbird Simkin has been migrating south by boat for a half-century. “In this boat it takes me six days — plus or minus a few hours — to go home,” he says. “Coming back, it’s 10 days against the Gulf Stream.”

Donald Brehm, a neighbor of Simkin’s for 20 years and sometime crewmember on Sea Fever, says these voyages are never routine milk runs. “He still runs against himself when we sail back and forth between Florida and Long Island,” Brehm says, laughing. “He tries to beat his previous best time. He’s very competitive with himself.”

Simkin bought the centerboard Scheel 45, one of about a half-dozen built, after Muriel died. A donation to the Coast Guard Academy in New London, Conn., it was “a mess” when he bought it, he recalls. “I ripped the boat apart and put it back together. It’s really a great boat now — a solid boat and very seakindly. I can go anywhere in it.”

Simkin invested 5,000 hours in the rebuild. He refinished the interior and rerigged the boat for single-handing with electric winches, a power anchor windlass, and a furling main, mizzen and genoa. The boat has an autopilot, bow thruster, GPS and electronic navigation gear. It’s easy to sail and maneuver. “There’s nothing to it, really,” he says. “When I’m sailing, I have very little to do except take the sail in once in awhile. I have electric winches for that.”

Though still spry, Simkin understands his limitations and the dangers of sailing alone. Under way, he seldom leaves the cockpit; he seldom needs to. In bad weather he heaves-to and goes below. “I don’t try to fight it,” he says.

The 30-year-old Scheel today is in Bristol condition. “Mac is a very, very meticulous man,” says Bob Wissmann, 76, of Sebastian, Fla., a retired Long Island boatyard and marina owner who has sailed with Simkin on a dozen voyages. “He takes very good care of the boat — not just visually but mechanically and electronically.”

Wissmann says the old skipper can be gruff at times and quite opinionated, but the two get along fine at sea. “He considers me his equal as far as sailing goes,” says Wissmann. That means he can offer an opposing view about what they ought to do and get a hearing.

“He’s a good sailor,” Wissmann says. “When I go off watch [and Simkin comes on], I sleep. I sleep well. That’s about the best recommendation you can give a sailor. I’ve never found him asleep on watch. That’s more than I can say about some younger guys we’ve taken with us.”

The son of Russian immigrants, Simkin grew up in the Bronx, where he acquired a passion for building model airplanes — hundreds of them. As a student at Haaren, a public aviation high school in Manhattan, he raced home-built rubber-band-powered indoor gliders to two world speed championships. He financed this hobby working for tips delivering drug store medicines, but some weekends he would take his money, rent a rowboat for the day at Throg’s Neck, and go fishing on the East River. While he banged around with clumsy oars on spring days, he would see young men glide gracefully by in small boats powered by sails. Simkin decided he wanted one of those. “They looked like the most beautiful birds sailing along the water,” he says.

The aviation student designed a 16-foot sailboat and presented the drawings to his science teacher, Walter Wachter, whom he knew to be a sailor. Impressed with what he saw, Wachter introduced the precocious Simkin to CityIsland designer and boatbuilder Del Barstow. “[Barstow] told me, ‘This is a very nice boat,’ ” Simkin says. “ ‘It will need a few alterations. Why don’t we build models of it?’ ”

The following spring Wachter invited Simkin out on his 32-foot gaff-rigged centerboarder and started teaching him to sail. “I sailed with him for the next 20 years,” Simkin says. “He was my very best friend until he died at 70. I’ve been boating for my whole life because of what this man did for me. He introduced me to boating and to a lifelong relationship of student and teacher.”

“Sailing is his love. It’s his obsession,” says Brehm.

Wissmann agrees. “Mac is a real sailor. That’s why he’s still sailing.”

“He’s a good problem-solver,” adds Brehm. “He rigged that boat so he could sail it by himself.” He adopts new technology, if it’s helpful. “He’s very savvy,” Brehm says. “He keeps on top of things. If there’s something he doesn’t know, he gets on the ham radio and asks.”

Simkin has raced Star and Atlantic class sailboats, cruised extensively, sailed across the Atlantic, and skippered his yacht Carastee in the 1960 Newport-Bermuda Race. The 635-mile race was notable for the 60-knot gale that forced him and others to heave-to for 13 hours and gave Carleton Mitchell his third straight Bermuda victory on Finisterre.

Simkin became a crack sailor, but instead of going on to design boats or airplanes or paint portraits — he had won a year’s scholarship to an art institute after high school — he went to dental school. There he learned to use his artistic talent, his skill in design and model-building, and his interest in technology to reconstruct mouths and jaws and teeth damaged by disease or accidents — often automobile accidents.

Simkin built a very successful practice, first in New Jersey and later in Manhattan. He taught at New YorkUniversity and became widely known for his work. Yet he considers the Nereia ketch he built 50 years ago behind his New Jersey home one of his greatest achievements.

“I built it like a dentist would, to a fraction of a millimeter,” he says.

It took him seven years and 14,000 hours. He would work all day at his practice, then spend most of the night working on the boat — sometimes sleeping just two hours. The 36-foot Nereia, a kit design that Herreshoff drew up for Rudder magazine’s “How to Build” series for amateur boatbuilders, was a “wonderful boat,” Simkin says. “It was the best-sailing boat I ever had. Herreshoff was an artist.”

Simkin, in his mid-30s then, met the venerable designer, talked to him about the boat, and even had the audacity to suggest changes in the cabin top lines to improve its aesthetics. Herreshoff didn’t think the changes would work, but Simkin incorporated them anyway.

“I went up to Marblehead [Mass.] to show him the boat, and he said, ‘It looks rather nice. It looks OK.’ Then, sitting in the cockpit later, he said, ‘I have to admit it’s absolutely gorgeous.’ ” Herreshoff told Simkin the workmanship on Carastee — named for Simkin’s children Carol and Steve — was the best he’d seen on one of his boats, bar none.

Simkin knew nothing about boatbuilding when he started, but he spared himself no pain in learning. It took him months to loft it. He built the masts, bowsprit, tiller and rudder first for fear he would be so drained after completing the hull that he might lose heart and never finish. “You need a lot of energy,” he says.

And ingenuity. He cast the keel in his back yard, designing and building the mold for it. He bent wood ribs for the hull in a steambox. Planking — shaping, twisting, fitting the 4-by-1-1/4-inch mahogany planks — demanded precision and patience, two of his strong suits. It took him three days to fit one plank and a couple of years to finish the job. “I thought I’d never live to see the end of the planking,” he says. He fabricated the pulpits and stanchions and many of the fittings himself.

Simkin launched his new ketch in Port Washington, N.Y., and renowned yachting photographer Stanley Rosenfeld photographed it. Designer John Atkins wrote him a letter saying it was the “finest amateur construction he’d ever seen,” Simkin says. The owner of Marshal’s Boatyard, who laughed when Simkin said he was going to build a boat, went through it while it was still on the hard. He was impressed, too.

The Simkins sailed Carastee together for more than 30 years. “Once I built that boat, I never worked in summer again,” he says. “I took two months off.” Later he extended their cruising to two months in summer in New England and two months in winter in Florida and the islands. After Muriel died, he sold Carastee. It carried too many memories. “It was something we owned together,” he says.

And sailed together, in good and bad weather. The couple was caught one year off Cape Fear, N.C., for 19 hours in 70- to 80-knot winds. They hove-to, the bow riding 25 to 30 degrees into the wave faces with the mizzen sail up and the rudder lashed to one side.

“We were both a little frightened — and seasick,” he says. They lay lashed into their bunks, getting up only to run to the head to vomit. Carastee took care of herself. “The boat was wonderful hove-to,” he says. “There was no one better than Herreshoff at designing boats.”

Simkin knows he might not be able to handle that storm today, not alone, so he is careful to pick the right weather window when he goes offshore. He has the forecast data at his fingertips on the computer.

“But it’s like anything else,” he says. “You never know. Anything can break. And if anything goes wrong, I’m just one person. An old man. That’s not so great.” Yet he doesn’t let it stop him.

“I’ll sail for as long as I can do it,” he says. “It’s keeping me young. I’m agile. My brain’s working. But you never know what will happen. You just live day by day.”

That’s another of his secrets to aging gracefully.