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On Wednesday, the morning of our first practice, it was blowing from the northeast at 18 and gusting to 25 knots across our anchorage—a typical Heineken Regatta day. Unlike my home waters on the West Coast of the U.S., when the prevailing Trades are blowing there’s little diurnal variation. In other words, the wind blows all day and all night. What you see is what you get.

As Team Boston enthusiastically prepared our Moorings 49 for practice, whitecaps flickered across the sea’s surface. Salaway snapped to her rode in the puffs. Our plan was to sail around the island and reconnoiter landmarks, currents, and wind, while practicing our boat handling skills.In a cautious mood, I suggested we weigh anchor and set the mainsail under power. No matter how you look at it, a 50-foot boat in 20+ knots of wind is going to have a lot of power in her rig going to weather. We pulled in a single reef, set the 110% Genoa, and pointed seaward.

The first leg on our around-island was an easy reach. I consulted my notes and confirmed that the faster water was along the beach. We sailed inside, watching the charts on my little ASUS notebook computer and eyed the water’s color along shore. The way was clear.

Our race instructions told us that a mark would be set about 1/4 mile offshore of Pointe du Canonnier on the Teres Basses peninsula. This meant that if we hugged the shoreline we would have to steer almost dead downwind to round the mark. Would the inside advantage compensate for the DDW wind angle?

We shook out the reef and reached to the waypoint. Brad drove while Bob trimmed the main. The rest of the crew stood by the winches. Team Boston’s lively discussion made for great fun as we tried to imagine sailing this line amid dozens of competitors. I made a note to watch boats sailing in the fleets ahead of us on this leg. We wouldn’t be taking any flyers on this, our first Heineken Regatta.

Once we rounded the location of the mark at Cononnier, we came onto the wind in the Anguilla Channel. Here, I had been told; the Anguilla Current flows from east to west and is strongest in the middle. Our strategy would be to hug the shoreline and short tack in the bays at Marigot, Grand Case, and Froussards.

With the wind at about 20 knots, I decided to see if we could carry the full main on the upwind leg. We shook out the reef, pulled on the outhaul, and tightened our halyards. These were the only controls we could legally use in the bareboat division. No matter how hard we pulled, the old tattered main looked like a bucket.

As we brought Salaway hard on the wind, she lay over on her rail and loaded up. I took the wheel while Bob worked the mainsheet traveller and sheet. I started feathering the boat, looking for a sweet spot that would get Salaway’s feet under her.

Salaway rounded up violently. “Bob, Bob, Bob, ease the main!” I shouted. Bob traveled down and I regained control.

“Bob, Bob”, I shouted again, “travel up and get the main working.”

I didn’t know it then, but in the days to come “Bob, Bob, Bob” would become a familiar incantation aboard Salaway.  As I look back on it now, that call must have become horribly enervating for Bob, but on the beats, it was his relentless attention to that big mainsail that made it possible for us to do as well as we did. In fact, as things turned out, Bob came to own that mainsail!

We started the beat up the Anguilla Channel staying along the shoreline at Marigot. We tacked in, watching the chart and water’s color. We noted the lifts, headers, lulls and puffs. On starboard, our course sheered away from the island coast, carrying us out into the current, waves breaking over the bow. On port, we plowed shoreward toward the rocks.

Tacking, tacking, tacking, we worked our way up the coast. The wind strengthened and we fought harder to keep Salaway on her feet. The Genoa trimming teams experimented with techniques and organization, improving with every tack. Our Special Forces muscle, Mike, Chuck, and Don, manned the winches, while Karen, Ana, Elena, Kara, and Monika, tailed and called trim instructions to the brute force grinders. Brad, Chuck, and I traded driving duties as we worked our way uphill. Communications and skill improved with every leg. We were almost looking good!

Then disaster struck.

In a gust the mainsail’s leech cord parted just below the first reef. The sail zippered open. The boom dropped. Jaws dropped. Eyes popped. It was our first practice and the boat was disintegrating before our very eyes!

Bob was first to see the immediate solution. “The tear is below the reef point!” he shouted, “Let’s pull in the reef one.”

Now our reefing practice in Santa Cruz paid off big time. I feathered the boat up while Bob eased the mainsheet. Mike leapt to the mast while Karen and Kara eased the halyard down to the first reef point. Mike shouted “Made!” Karen and Kara started cranking the halyard for tension while Ana and Chuck started pulling on the clew’s reef line. The boom rose to the first cringle and a few cranks later we were sheeted home and sailing again. Nice work!

Next we settled into problem solving mode. We were going to have to deal with a shredded mainsail and deal with it fast. We hailed Moorings on VHF 77 to no avail. Fortunately, most of the crew had fancy cellular phones. We raised the charter base on the phone and explained our situation.

Moorings suggested that we return to Simpson Bay anchorage by 1500 and they would pickup the mainsail for repairs. My pleas for a new mainsail fell on deaf ears. The best they could do they told me, would be to tape the thing together overnight.

I calculated distances and wind direction. There was no way we could continue around the island. We would remain blind to the island’s windward side and the mark at Tintamar and that would cost us come race day. As we turned tail and retraced our steps to Simpson’s Bay I contemplated our situation. Was this an ill omen? Was our little ship accursed? I scanned the sky for an albatross.

As promised, Moorings showed up to retrieve the torn mainsail. Team Boston settled into post-race party mode while the Moorings manager, Corrado, and an assistant dismounted the main. I did my best to enjoy the proceedings, but the equipment failure gnawed at my brain. We had yet to begin racing and equipment issues were already taking a toll.

At sunset I used our dinghy to shuttle Team Boston to shore where they would dine, party, and sleep in their hotel rooms. I settled in for the night aboard Salaway and an early morning re-rigging the repaired mainsail.

Thursday morning marked our final practice day. Moorings had arrived early. I shuttled them to the boat and helped re-mount the mainsail. Relief washed over me when I saw that they had stitched the tape and repaired the leech cord. With a little luck the sail would last the series.

Team Boston’s plan was to make the last practice a short one during which we would stand off Simpson Bay to review the basics and starting line maneuvers. The crew arrived at about 1030 with a McDonalds breakfast and double-hash browns. That hit the spot!

In 15 to 18 knots wind with stronger gusts, we hoisted the main for a look. All I could think was that we needed to find a way to flatten the thing. One solution was to re-rig the outhaul to add purchase and tension to the loose-footed sail. Then we cranked the halyard until the four turns on the winch slipped. My spirits rose as creases formed in the luff and foot.

We practiced for about three hours. Team Boston was getting to know the strings and it showed. It soon became apparent that Bob would be our co-captain. He was our most experienced crewmember. He was competent, knowledgeable, and he could be easily heard from his middle position tending the mainsail.

Team Leader Brad and his first mate Karen took me to the stern and informed me in no uncertain terms that I would be driving the starts. This was not a discussion. It was an order. I had hoped to have Brad drive conservative starts with me coaching. Now the onus for competitive starts would fall on my shoulders. I felt my knees wobble as I contemplated what we now knew would be 20 50-foot bareboats starting in 20 knots of wind. So it goes.

We decided that Karen would ride the bow during the starts, calling traffic and distance to the line. Brad would manage time and be my extra set of eyes. The rest of the crew would work the cockpit, trimming Genoa and main.

Our last pre-race task was to drop off the dinghy with the Moorings support boat. I was glad to see that thing gone. As we set the anchor I took Brad aside. I knew I was about to commit a sacrilege but someone had to do it. I “suggested” that he ask the crew to curtail their partying on this one night. I said, “Don’t drink too much and get to bed early. We need to be in the starting area by 0830. The start will be intense and the around island course will take most of the day. Short tacking up island in 20+ knots of wind will be both physically and mentally demanding.”

I knew full well that my suggestion was not in keeping with Team Boston’s habit. I studied Brad’s face, waiting for the sh_t to hit the fan. To my surprise and everlasting gratitude, he nodded in solemn agreement. I had no idea how he would rein them in but if anyone could…

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