Cruising

How a Racer Learned to Cruise

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Those who can, don’t teach

After working together at SAIL for two years, my coworker Christa asked me if I’d teach her to sail. Having never “learned” how to sail with either a coach or in a classroom, though, I knew my limitations as a teacher. Christa’s idea of sailing didn’t involve having orders barked at her or having someone else do everything on a boat while she simply tried to stay out of the way, which is how many people learn how to race. She wanted to legitimately learn how to sail. To get her properly educated, we contacted Offshore Sailing School, known for teaching sailors of all abilities.

We left Boston in the middle of January and traveled down to Captiva Island on Florida’s west coast to spend a week at Offshore. We both had goals for the week: I wanted to get more comfortable at the helm, and Christa wanted to learn enough to take her sons out sailing in Boston Harbor. She wanted to know what it meant to trim the main, to tack and to gybe. She wanted to learn the difference between a rope and a sheet, and she wanted to talk to the person who came up with that concept. That guy had some explaining to do.

I’m a sailor—get me out of here!

On our first day we met Heather McIntosh, the Offshore instructor responsible for the Basic Keelboat portion of our course. She was to spend two days with us both in the classroom and out on the water. I was not excited about the classroom portion of the course. If there’s something for me to learn about sailing, I figured I’d learn it on a sailboat, and when Heather brought up the first slide in her PowerPoint presentation, I groaned: there on the screen was a diagram of a sailboat, under which in bold print read the words, “What is Sailing?”

Luckily, it only took about five more minutes for me to realize I could learn a lot from Heather. A circumnavigator and boat captain, Heather had just returned from Ireland by way of Grenada; she had sailed doublehanded from the Caribbean to New Zealand, was well-versed in celestial navigation and knew her way around a diesel engine. In no time I was hanging on her every word.

Three hours later, it was time to go sailing on one of the school’s trademark Colgate 26s. School co-founder Steve Colgate designed the Colgate 26 in 1996 to replace the Solings that were Offshore’s training boats for almost 30 years. The boat’s stability and roomy cockpit make it ideal for teaching, while its performance makes it popular in racing and cruising circles around the world. We rigged the boat and Heather navigated us out into the Pine Island Sound. “Alright, Christa, you’re up,” she said.

Watching someone take charge of a boat without any prior experience is somewhat akin to watching a baby learn to swim for the first time. The baby grins and laughs and enjoys being in the water, but the experienced swimmer knows the baby could drown at any moment, and anticipates disaster. Christa wasn’t nervous at all. She was both completely at ease and happy to be discussing what she had learned earlier in the day. While I was committed to letting Heather be the instructor, it was difficult for me to not tell Christa to hold the tiller differently, to position her body differently, to do everything differently.

“Alright, so now we’re going to practice a tack,” Heather said. I loaded up my winch and got myself into position.

“OK, we’re tacking,” Christa said.

“Ready,” I said.

We then sailed on for another four boatlengths.

“Christa?” Heather asked.

“Yeah?” Christa responded.

“Let’s tack.”

“OK. “

“Ready.”

Another four boatlengths went by.

As it turns out, tacking is a learned action. It doesn’t really come naturally. But once she got the hang of it, we were on a roll. Almost too much of a roll.

Once we were comfortable with tacking, Heather had us turn downwind and cruise along Pine Island Sound toward Sanibel Island. Christa was still smiling, joking with Heather about everything from having babies to sailing around the world. The boom was far off to starboard, and we were running dead downwind.

Whump! The boom flew across the cockpit with a deafening sound as we crash-gybed. I looked at Christa, her hand still on the tiller. I wanted to shout, “Watch where you’re going or else we’ll do that again, and someone could get decapitated!” But, again, I was committed to letting Heather be the instructor on this boat.

“We didn’t mean to do that. It happened because we are sailing by the lee, and we need to avoid that. Let’s try avoiding that,” Heather said, calm as a cucumber.

“OK,” said Christa.

Whump! Another crash-gybe. I was going to need a Xanax.

We went through another three or four unintentional gybes, to the point where I stopped worrying so much about them and just kept my head low. After the last one, Heather finally said, “OK, I think we’re finished with the unintentional gybing now,” and gave Christa clear instructions on using the compass. I moved from the jib to the main, so I could control the sail during gybes when Christa called for them. After that, well, they call it smooth sailing for a reason.

Despite the gybing drama, Christa’s smile was as broad as when we began. She was enjoying herself and having a great time on the water. I thought about my own childhood in a sailboat, when I was constantly worried I would broach, capsize and then perish. I saw the value in Heather’s calm demeanor, her “it happened but it’s not a big deal” approach. While her first priority was safety, she also wanted Christa to enjoy herself—and it was working.

Gimme the stick!

We had been on the water for an hour and a half when I was handed the tiller. I felt ready for it. Christa took my place trimming main, and we settled in for some upwind sailing.

For all the time I’ve spent on the water, I’m not often at the helm. I’m generally in the pit or on the foredeck, where I feel comfortable and in control. At the back end of the boat, I’m generally quiet and tense. But after a morning spent learning the “math” of sailing, I felt more comfortable. You might even say I was enjoying myself. I was in charge of the boat, and we weren’t going to perish.

My hour and a half of tiller time went by too quickly. I was soon comfortable moving through the points of sail, and talking my crew through tacks and gybes with the same ease I ask my co-workers about their weekends. When Heather asked if I’d like her to take the tiller and navigate us back to the dock, I told her she was fine where she was: I had this one. I smiled to myself as I docked the boat effortlessly. In any other situation, I would have dropped the tiller like it was on fire to get out of docking. But here, whatever. Not a big deal.

Our two days with Heather flew by. We practiced quick-stop and quick-turn recovery drills around Captiva in the Gulf of Mexico while dolphins danced in our wake. The longer we were out on the water, the more aware I became of the overall strategy of sailing. As a racing sailor, your job is to make the boat go fast and beat everyone else, but through Offshore I was learning to sail smart, not just fast.

Breaking out the big guns

After two days of sailing with Heather, we went to work with Clay Mathias, an instructor who’d been on the sailing team at St. Mary’s College in Maryland. Clay’s job was to get us to both sail and dock a 50-foot Hunter, at the same time reminding me that although it may be impossible to capsize a boat of this size, I could still cause some serious damage.

Our classroom time with Clay focused less on points of sail and wind shifts, and more on diesel engines, anchor placement and navigation. Bigger boats lead to bigger waters and bigger responsibilities, so much of Clay’s teaching dealt with those aspects of sailing that don’t involve having a tiller in your hand. To teach the importance of boat logs, for example, he showed us the log from a race in which the wind had gone from calm to gale-force in just four hours. Pretty dull stuff, I thought, until I realized we were looking at Steve Colgate’s personal log from the 1979 Fastnet Race. “Is that what I think it is?” I asked.

“Oh, yeah. Steve has some stories.”

Indeed he does.

The chilly wind that had defined our time with Heather was now becoming noticeably warmer. It was 5 knots at best each afternoon, so our focus turned to anchoring, compensating for prop walk, and otherwise handling a boat so massive it would intimidate even the most competent sailor. Crawling around belowdecks, Christa and I channeled our inner gearheads and dissected a diesel engine.

“Do you think you would know what to do if you had air in your fuel lines?” Clay asked Christa.

“Are you serious?” she replied, wiping a strand of hair out of her eyes with a greasy finger. “Clay, I can bleed the air out of those lines in my sleep.”

Clay just nodded, amused by the authority with which his newbie student took charge. We knew our stuff.

On our last day I brought the Hunter into the marina to dock it. A group had gathered at the end of the gas dock to gape at some manatees, and they all tipped their hats to my instructor as if to say “good luck with that one.” As we approached, I kept my eyes on the dock and listened intently as Clay told me how much room I had, at the same turning and shifting in response to his hand commands from the bow. Afterward, with the boat safely tied up, I asked Clay if he had been nervous having me at the helm.

“No,” said. “I knew you had it all along.”

Strangely enough, so did I.

Lessons learned

No matter how fast a sailboat is, as skipper you can’t be the only one competent to dock it, maneuver it through a man overboard drill, or fix the engine’s fuel intake valve. Fortunately, Offshore Sailing School is a school for sailors, not just for people who want to learn how to sail. Their education is challenging and forces you to step up and take control, no matter your experience level.

Christa and I went into the week with different expectations, but the two of us both met and exceeded the goals we set for ourselves. She came away confident she could take her sons out and teach them about sailing. I came away confident I would be a stronger, smarter crewmember, able to both dock a 50ft boat and rescue an overboard skipper. The experience changed both of our attitudes toward sailing, giving us a greater appreciation for the sport as well as the pastime.

Standing in the Miami airport, a young man wearing a Mount Gay Rum hat stood in front of us arguing with the check-in clerk about how to get down to Key West for race week. Christa tapped my elbow with a chuckle.

“I’ll bet he doesn’t know an engine block from a hole in the ground,” she said.

“He doesn’t know a keg stand from a kedge off!” I responded.

Oh, our instructors would have been so proud!

Photos by Christa Madrid

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