Learning the Art of Seamanship

There are lots of ways to make mistakes on boats. The right way is to make them over time, so you can learn from them.
Fatty Goodlander sailing his way to Tahiti
Fatty Goodlander stays hard at work a dozen miles east of the Gambiers 40 days into his fourth circumnavigation, with eight days to go until reaching Tahiti. He says that offshore sailing can be among the most labor-intensive lifestyles imaginable—and at the same time, one of the most fulfilling. Courtesy Fatty Goodlander

Too Tall,” as I call him, made a modest living banging nails in Lynn, Massachusetts, working in residential construction. We met while shooting pool on Revere Beach. He was intrigued to learn that I was building a 36-foot ketch from scratch. 

“What for?” he asked. 

“To make the big, fat circle,” I explained. “And to be free, really free, not consumer-­choice free.”

A few weeks later, during a backyard barbecue in Swampscott, Too Tall noticed a trailerable sailboat in the host’s two-car garage. It was an O’Day 19. His buddy told him that he didn’t have the time to sail it, and, worse, his wife was getting a new AMC Gremlin. They needed the space in the garage.

Too Tall left with the boat on his trailer hitch, to both their surprise. “Got it for a song,” he crowed to his wife while showing it to her in their driveway.

“Oh, dear,” she moaned. “That’s exactly what a pregnant wife needs: a hole in the water her husband pours money into.” 

Truthfully, it was a stressful time. His wife was worn to a frazzle, getting ready for the baby and taking Lamaze classes while working a full-time job. Worse, Too Tall knew that he was drinking too much while trying to cope with all the changes. He decided to cut down on the booze and concentrate on supporting their rocky transition from couple to family. 

The following week, his wife volunteered to re-sew the mainsail using a new, sun-resistant Gore-Tex thread she’d read about in a women’s magazine. Meanwhile, Too Tall assessed the centerboard. The previous owner had snapped it and lost the rudder in a storm. Too Tall came down to use my band saw, to rough-cut the shapes in marine plywood. 

“How long do you expect to be gone?” he asked, staring up at the half-finished hull of my 36-foot Carlotta.

“Forever, I hope,” I told him. 

“Aren’t you scared of drowning?”

“Aren’t you scared of driving drunk?”

“Touché,” he said.  

I didn’t hear much from him in the next few weeks. Later, I learned that he had a buddy who spray-painted trucks. The O’Day ended up with black topsides, a red boot top, and blue antifouling. 

For his birthday, his wife presented him with fitted sheets she’d sewn. She’d figured out where he kept the companionway key and measured for them. 

“We’re gonna need an Igloo cooler,” she mused afterward. 

The word we made Too Tall smile. 

Construction work took most of his time, and it was 18 months between buying his boat and sailing it. Naming the boat became a family matter as well. Too Tall rejected his wife’s Titanic Too idea and went with a suggestion from Martin, his just-beginning-to-talk son. 

The first time he sailed Mighty Mouse, Too Tall’s main halyard broke, but he managed to get back to the boat ramp under jib alone. The second time out, he took a cockpitful of water in a gust. From then on, he never fully cleated off his mainsheet. 

During the third sail, he ran aground, but, luckily, sand is soft. After that, he always taped a photocopy of his chart to his aft cabin face, right under the through-bulkhead compass he’d purchased on sale at Bliss Marine. 

He started racing at a local yacht club, and he was utterly amazed at how slow he could make a sailboat go. After one race, while he was ashore at the awards ceremony, the boat dragged and damaged its new rudder. So, Too Tall returned to my boat shed with questions about anchor type and ­whatever scope was. 

One evening, when his wife’s parents were visiting and they had a babysitter, Too Tall picked up his wife at Constitution Marina and sailed her to the Boston fish pier for dinner at the No Name Restaurant. She felt good tucked into his shoulder as they sailed. 

The O’Day eventually was replaced by a 22-foot Westerly Nomad—not a racer with its twin keels, but perfect for the mud mooring he’d wrangled in Winthrop. Then came the big breakthrough. With Martin now 5 years old, the family chartered a 32-foot sloop out of Long Bay, St. Thomas, and had the best 10 family days of their lives. His wife loved the Virgin Islands, Too Tall loved the trade winds, and Martin took to the water like a gleeful fish.

The first time out, his halyard broke. The second time, he took a cockpitful of water in a gust. From then on, he never fully cleated off his mainsheet.

Many of the local ­liveaboards in the Virgin Islands anchorages had kids, and Martin acted as the ­couple’s passport into many ­joyous cockpits aboard cruising yachts from all over the world. Sailing back to Charlotte Amalie on St. Thomas as the sun set and Martin napped below, Too Tall’s wife whispered into his ear: “Wouldn’t it be wonderful if we could make this moment last forever?” 

A Contessa 32, designed by David Sadler, had been damaged against a seawall in Scituate, Massachusetts, and the insurance company wanted to offload it. Too Tall didn’t know anything about fiberglass, but a few months later, he was an itchy expert. Their first family cruise was to Maine, where they blew out their genoa while sailing overcanvassed in a squall off Portland. Too Tall immediately revamped his reefing system, which worked flawlessly during the next summer’s cruise to Mystic Seaport in Connecticut. 

By the time Martin went off to the California Institute of Technology on scholarship, the couple had already crawled “The Ditch” to Florida a couple of times on their Carl Alberg 35. From there, it was an easy jump to the Bahamas and, eventually, to wandering the Lesser Antilles. There, they bumped into many of our dear friends on St. John, in the US Virgin Islands. 

During this entire time, Too Tall made just about every mistake in the book, from running over his dinghy painter to leaving a dock without unplugging his shore cord. Once, while dragging in the Turks and Caicos as a tropical wave passed ­overhead, he’d been unable to cast off his anchor because of the splice at its bitter end. The following day, he’d cut off the splice and never belayed his anchor rode again without ­being able to cast it off instantly under load. 

But, dear reader, this ­column isn’t about Too Tall and his wife or how much fun they had, eventually, hanging in Panama’s San Blas archipelago and cruising along the east coast of Central America. 

It’s actually a column about Duncan and Barbara. 

Duncan, a just-retired attorney specializing in international law, was living in Johor Bahru, Malaysia. He’d nurtured a dream for decades of cruising offshore. He knew exactly the kind of boat to get. He found one listed for sale in Langkawi. It was almost brand-new, having spent most of its life on the hard at Rebak Island. 

Barbara knew nothing of boats, but what was there to know other than how to make a piña colada?

Duncan didn’t like the idea of heavy weather, so he had his sailmaker stitch up an asymmetric spinnaker along with one of those newfangled cruising chutes with the strings and holes. The thing that frustrated Duncan most was how long all the Malaysian shipyard workers took to mount stuff. His weather window was almost gone by the time his davits were installed, his cockpit fridge was chilled, and the new instrument array at the helm was blinking on. 

He asked me for advice. “Take it slow,” I said. “Just sail a few miles down the coast to a safe harbor, then venture forth as urge, experience and expertise dictate. Don’t scare yourself and, especially, don’t scare your spouse. Baby steps will get you to Cape Town, South Africa, faster than anything else.”

He intended to follow my advice, but those damn dawdling workmen. He’d pored over Jimmy Cornell’s books about weather windows. It was now or never. 

So, Duncan and Barbara set off to cruise Indonesia and then hop down to Australia’s remote territory of Cocos Keeling, without ever having overnighted on their boat. Hell, without ever having sailed their boat out of sight of land. Or within sight of it, for that matter. 

Within 12 miles of leaving, a wave boarded them (current against wind) in the Malacca Strait—and their $8,000 inflated life raft was trailing astern. The only thing Duncan could figure was that the factory-made bracket he’d purchased with it had been defective. How else could the raft have escaped? 

It was too rough to bring the dinghy on deck. He cut it loose. Barbara didn’t say anything at the time, but this scared the bejesus out of her. If they’d lost their life raft in the first two hours, how long would it take to lose the entire boat?

From that moment on, Barbara took to her bunk and prayed while silently resolving: marriage, yes; suicide by saltwater, no.

Their brand-new lithium batteries went flat, just like that. Without electricity in the house bank, they couldn’t use their autopilot and had to hand-steer. In a real blow. With the wind gusting into the mid-20s.

They didn’t have time to think, really. Only to survive. Sleep was impossible while hard on the wind. They’d become complete numbskulls but didn’t have the experience to realize it. All the hatches leaked—poured water below, really, much of it directly onto the navigation station, where, one by one, their new electronics failed. They wondered: How could so many different suppliers sell them so much defective equipment? Their smartphones were waterproof, weren’t they? 

Not that their smartphones worked. They were out of cellphone range. Or didn’t have the right SIM card. Whatever.

Damn, it was dark at night. They couldn’t get a weather report. When would this horrible wind stop? Thank gosh for their Garmin GPS. At least they knew where they were. Right by those tiny blue dots on the chart.


The sound a 30,000-pound fiberglass vessel makes as it crunches up on a coral reef is horrible, and, of course, expensive. Within 72 hours of setting off on his long-awaited Indian Ocean cruise, Duncan called me and whispered in a still-quivering voice, “It’s a lot of work, isn’t it?”

“Offshore sailing is the most labor-intensive—and for some, the most fulfilling—lifestyle imaginable,” I replied. 

“Barbara doesn’t like it,” he said. 

Ah, yes. Blame it on the wife. How convenient. 

“It’s not relaxing at all.” 

I held my tongue. 

Yes, Duncan had a law degree and a pocketful of gold, but he little common sense and absolutely no seamanship. That can’t be purchased. It has to be earned. 

The bottom line: Duncan didn’t make one-hundredth of the mistakes that Too Tall had made. Duncan merely made them all within the first 48 hours, amid poorly charted foreign shores, while surrounded by rocks. 

“Don’t make any major life decisions right now,” Carolyn advised Duncan. “Relax. The scrapes on your hull can be fixed. Things will seem better in the morning.”

They haven’t called us back with their ultimate decision, but we know what it will be. They scared themselves silly. And that fear will take a long, long time to wash away. 

So much for baby steps. 

Isn’t there a middle way? A path between a lifetime of learning and ­absolutely none? Of course. We know many happy cruisers who, within a year or two of thoughtful coastal sailing, safely head offshore. 

Here’s the distillation of my 63 years of cruising the world: Seamanship matters. Money and BS, not so much.