My sailing experience was sufficient to convince The Moorings that I was qualified to charter a 43-foot sailboat out of their port in Syros, Greece, but – frankly - I was not so sure. I had single-handed in Maine fogs, sailed 7,000 Pacific Ocean sea miles and – at age 21 - even commanded a 40,000 ton U.S. Navy tanker as Officer of the Deck. Still – I worried. Greek waters are susceptible to occasional Meltemis – sudden gut-churning winds. I would be mooring my vessel in crowded seaports under the discerning eyes of professional mariners. I had also recently turned 63 and, with arthritis threatening, had lost the agility of my youth. Perhaps a sailing school was in order?

My research suggested that Offshore Sailing Schools, with bases in Tortola, the Florida Keys and New York City (the Bronx) was the right fit for me. The Bronx school ship would be a 46-foot Hunter sloop with accommodations for a captain/instructor and three students. It took little convincing to sign up my old friend, Terry Vose, and my cousin, Val Hart, to join me. On a Sunday night at summer’s end we joined up in a dormitory suite at SUNY Maritime College and turned in early.

The next morning we found the Hunter at her mooring. I have sailed yachts up to 38 feet, but they were old style – narrow and graceful of sheer. This boat is beamy and she’s at least half again larger. She looks like an aircraft carrier. How will it be to maneuver such a beast in tight quarters? When I express my concern to Captain Tom Ruegg, our instructor for the next five days, he tells me: “Don’t worry. She looks big now but in a day you’ll realize she’s just another sailboat.”

Captain Tom exhibits a genial expression under thinning silver hair. He wears a light blue Offshore Sailing School polo shirt and tan shorts that expose powerful arms and legs. He appears good-natured, almost avuncular, as he looks us over.

Of the three of us, I am the most experienced. My mission is to relearn skills that have become rusty and to acquaint myself with systems – refrigeration, generators, GPS, pressurized water and multiple heads and showers - that are rare on the classic boats that I have sailed in the past Terry has crewed aboard a large schooner in Greece and served on a 60 foot motor yacht from Southampton, England to the Mediterranean - but that was many years ago. Val has the least experience, limited to sailing small boats in Maine.

“I was anxious when I boarded the Hunter,” he recalls. “I saw a lot of lines. There was a Genoa – not a simple jib. There was a main sail that furled into the mast. A huge wheel. The instruments were unfamiliar. I wanted to feel competent as a crew member and I was afraid I wouldn’t measure up.”

On the first night we sail into Manhasset Harbor and anchor. Captain Tom brings up “the puck” – a hand-bearing compass - and asks us to take sightings on three prominent landmarks and plot our position on the chart. After nearly an hour of fumbling, we agree on a spot where the lines of bearing cross. When we plot a comparable position with the GPS, the two are within a pencil line of each other.

“That’s a perfect example of hands-on learning,” says Tom. “You mastered the hand-bearing compass and the GPS in half the time I would need to explain it. You worked cooperatively, you solved a problem and you got the answer. Nice going.”

Tom sets us at ease with his positive encouragement and relaxed manner, a technique he evolved during 28 years of teaching in public schools. “If you’re too strict you destroy your students’ willingness to learn,” he says. “I have no rigid standards. I try to teach at the comfort level of my students.” Tom seems made for this job. He built his own small sailboat when he was 15, served in the Navy and later earned a master’s degree in education. He has sailed the Atlantic, the Caribbean, the Pacific and the Tasman Sea. He began instructing with Offshore Sailing Schools in the mid-nineties and now holds all the certificates offered by the United States Sailing Association. He is 65 years old. “I never want to stop sailing,” he tells us. “The ocean is the last place in the world where you have total freedom to explore and try new things. The ocean is never the same. It is infinite.”

On Tuesday, at a god-awful hour way before coffee or breakfast, Tom shows us the Hunter’s through-hull fittings and goes over the fine points of our 70 HP Yanmar diesel. We check out the fuel, electrical and cooling systems. We learn to inspect the belts, the fluid levels and how to look for signs of problems.

“If you notice black smoke from the exhaust the fuel mixture may be too rich or perhaps the injectors are leaking. If you see gray smoke there’s water entering the manifold somehow.”

Our goal is to pass three written tests - basic keelboat, basic cruising and bareboat cruising – to be certified as bareboat charter captains. All the information we need to know is carefully laid out in three books – rich with illustrations and review sections – which we studied before boarding the Hunter. Today, we take the basic keelboat test and wait anxiously for Tom to grade us. We all pass. Still, this is just the first hurdle – the others will be much harder. Tom seems to read our minds.

“Don’t worry about the tests! You have this great boat at your disposal. Let’s go sailing. Your hands and feet will tell you more than any book can.”

We set out from Manhasset and glide under an azure sky. A small Bimini provides shelter from the sun. The winds are light and variable – almost non-existent – but Tom insists on sailing rather than motoring. We are making a knot and a half over the ground, more by the outgoing current than the wind. Tom gives informal pop quizzes as we steer our course. “What kind of weather might accompany those clouds on the horizon?” “How many international distress signals do you know?” He shows us how to set up a DR plot and take bearings on a confusing array of landmarks. Is that a radio beacon over there? Which stack is that? Finally we plot our position - then compare it with our GPS. We are within a half-mile! In the late afternoon, we set the jenniker and proceed down Long Island Sound under a glorious spread of sail. Behind us, the horizon thickens with cloud over the distant Manhattan Skyline. The wind freshens and the boat picks up speed. Five knots. Six knots. Nine knots.

“Take in sail!”

Captain Tom and I man the foredeck. We slide a long sleeve over the Jenniker to douse it. Suddenly, with a loud pop, a turning block that controls the port sheet comes loose. Terry keeps us on course. Val tails the wayward sheet. Tom and I subdue the jenniker - now a long snake writhing in the gathering wind.

“Good job, men,” says Tom, “you’re acting as a real team.”

As we enter Huntington Bay, with Terry at the helm, the wind flukes off the land.

“Bring her up, Terry,” says Captain Tom. “Check the telltales. Okay, fall off. Can you feel it? The tiller will wiggle when everything is right. The boat talks to you. Listen to her.”

As we anchor, Tom drills us on the fine points of using the windlass and backing slowly under power to lay out the proper scope of chain.

Wednesday dawns crystal clear with little wind, so Tom decides to teach us to maneuver in tight places. We motor into crowded Centerport Harbor and find an empty pier.

“Plan your action,” he tells us. “Where’s the wind coming from? What about the current? How will you approach the pier? What lines will you use? What’s your escape plan?”

I steer. Terry mans the fenders. Val holds a mid-ship spring line ready to step off and secure the boat. I approach the pier gingerly, barely moving. I begin to swing the wheel.

“Not yet,” Tom says. “Wait until it seems the bow will hit the pier. Wait… Now.”

This is going to be a disaster, I think. I’m used to boats with full keels that respond sluggishly to the rudder, but the Hunter pirouettes on her fin keel and slides gently alongside the pier. Val steps off and makes the breast line fast. Tom gooses the throttle, swinging the boat tight against the dock.

“Easy as that,” he says.

Tom knows that Terry and I plan to sail in Greek waters where vessels tie up stern-to in what’s called a Mediterranean moor. This requires dropping the anchor and backing into a narrow space between other boats. Tom teaches us to face aft so the wheel turns in the direction we want to go. We learn that torque from the propeller – called “prop walk” – initially turns the Hunter to port regardless of the rudder’s position. Once she gains momentum, we turn her back on course, resulting in an S-curve that we control with precise inputs from the helm. We become comfortable with generous applications of throttle.

In the afternoon, we run man-overboard drills, mastering what is called the “quick stop” technique; we tack and gibe the Hunter, and learn to balance her on course with sail trim alone. Continuing on to Stamford Harbor, we set up a DR track and monitor our progress until we are adept with parallel rules and dividers. We enter the harbor under sail and pick up a mooring without help from the engine.

Thursday is a big day – three hours of tests on basic and bareboat cruising. Dawn finds Val tying knots on a stanchion, his book open beside him. Terry goes over notes, sprawled on his bunk. Tom and I prepare breakfast. With the dishes cleared away, we bend over the test sheets. All of us pass, even Val who has made up for his lack of experience by hard study. To celebrate we sail off our mooring and head out to sea in a freshening breeze. Val steers while Terry and I lay out our DR track to Oyster Bay, almost due south across the sound. I calculate the current set and drift, add an offset for leeway and give a course to Val.

“Are you sure?” the captain asks.

I find I have laid off the current vector one eighty degrees out.

“There are no mistakes, just leaning experiences,” saysTom, which has become a mantra during the voyage.

“We were on a broad reach,” Val recalls of that day. “I felt it all begin to come together. I felt the movement of the boat. I could anticipate the bow swinging because of the waves on the quarter. I was making the right adjustments, keeping her on course.”

We sail into Oyster Bay under gathering clouds, Val still at the helm. The wind is steady from the south, Val steers high into it.

“You’ve got to pinch up and yet keep her moving,” says Tom. “You’re riding the wind real good. It’s a feel and you’ve got it.”

“I was very happy with the captain,” Val will tell me later. “He was courteous. He was comfortable to be with, encouraging. He made me feel that I can take risks. I asked a lot of questions but it seemed like he could have listened to them and answered them until hell froze over.”

We tack into the harbor under threatening clouds, foul weather gear at hand. Soon, lightening streaks a lead-colored sky and rain spatters the decks. We grab a mooring with NOAA weather issuing a severe thunderstorm warning. By seven-thirty, the storm has passed and we’re on deck, sundowners in hand, toasting our having qualified for three U.S. Sailing certificates.

On Friday, we sail west up the sound in heavy rain and fog. Rain falls like white buckshot, dimpling the sleek black ocean. A sailboat follows in our wake – a slight thickening in the fog. We post a lookout and blow our horn periodically as the visibility closes to a few hundred yards. For three hours, we take turns steering and plotting electronic fixes every half hour and modifying our course as necessary. When the fog finally lifts, find ourselves headed directly for gong 23 off Execution Rocks – six miles from our base in the Bronx.

“This has been a good learning experience,” says Captain Tom. “Once again you teamed up well.”

After we pass under the Throgs Neck Bridge and moor off Fort Schuyler, Tom holds his last tutorial – a review of all the Hunter’s systems. He holds up the owner’s manual.

“This book is the Bible. You’d be a fool to go to sea without knowing about all the systems in it. On land, we’re used to turning a switch, opening a faucet, plugging in an appliance. We take water, fuel and electricity for granted. If there’s something to fix, we call a repairman. At sea, you bring all these life support systems with you. You’ve got to know how they all work and you have to be the repairman.”

By now we’re familiar with most of the systems but the captain takes us through each one, breaking them down into their separate parts - the inlets, piping, pumps, filters and outlets. Tom is a trained engineer and he’s in his element as he discusses each component in great detail.

That night, snug at our mooring, we review our experience. For me, the big boat’s maneuverability has been a revelation. I feel confident about our upcoming charter in Greece. Terry feels ready to handle the navigation and the myriad systems he will confront aboard the Moorings 43. But for Val, the voyage has been even more fulfilling.

“It was in some ways life-changing,” he tells us. “Everything you learn is applicable at that moment as you are moving through the water. You can see immediately what you’re doing right and what you’re doing wrong, so you learn quickly. And I was on a voyage with others who knew more than I did, but we all supported each other. It boosted my confidence not just about sailing but about my ability to explore other areas of knowledge – to try other things.”

Saturday morning, before leaving the boat, we work in unison – washing the decks, stowing gear, shutting down the systems. I go on deck to check the mooring bridle. I find two of the hatches are open. As I bend down to close the first, Terry reaches up from below and secures it from the inside. As I move toward the second hatch, I see Val’s hand reaching to close it. We have learned to think and work together – almost reading each other’s minds. Perhaps, after all our training and study, this is the ultimate lesson Captain Tom wanted us to take home.