Holy Cannoli! I like to sail

The purchase of a Cal 22 completed the author’s transition from power to sail. Photo by Tricia McGrath

By Tricia McGrath
For Points East

I am not certain exactly when it happened, but on a beautiful Sunday morning, late in the summer of 2002, I decided I really liked to sail. I was still not fond of heeling more than 10 degrees, but I had gone past the point of believing that any higher degree of heeling would mean a one-way ticket to Davy Jones’s Locker. For me, this was quite an accomplishment.

I found myself paying close attention to the sound of the water splashing on the hull. It was serene. Nature seemed to come alive when it was not competing with the sounds and smells of an outboard motor. But it took many years for me to become sufficiently comfortable with the motions of sailboats – and the theories behind their designs – to be able to focus on their beauty. However, from the time I was a child I’d been fascinated by sailboats, from daysailers to Tall Ships. Their sleek designs and ability to use the wind for propulsion had captivated me.

It all started with my grandfather.

I remember the first time I visited the State Fish Pier in Gloucester, Mass., with my grandfather. Two beautiful – and huge – schooners were tied up, waiting for supplies. I could not imagine how such vessels could move from port to port with all of their masts, sails and lines. The crew of one of the vessels raised the mainsail, which immediately filled with thick, foggy air. The captain held the wheel while crewmembers untied the lines. It was fascinating to watch.

Each sailor had his job to do, and it was obvious they’d done them many times before. There was little drama associated with their leaving the harbor. A few words spoken, a few hands pointed, and the vessel was headed to the open sea.

I watched with amazement as a second sail appeared on the bow and the wind filled it. I was certain that the ship would tip over and sink to the bottom. That, of course, did not happen. The windship picked up speed, she sailed past Ten Pound Island, then glided well offshore past a treacherous rockpile, becoming a black dot on the horizon just past the Dog Bar Breakwater.

My grandfather was the bridgetender for the Blynman Canal Drawbridge over the Annisquam River in Gloucester, and he knew the crews on the local fishing boats. They all waved to him as they headed out to the fishing grounds. And then, on the return trip, greeted him with a thumbs-ups or a thumbs-down, depending upon the volume of their catch. My grandfather and I were often invited to the State Fish Pier when the boats came in, to have a mug of coffee with the captains and crews, and watch as the fish were removed from the holds by the lumpers.

More often than not, these holds contained pogies. And the smell of dead pogies was, to me, a blend of putrefying fish guts, old rotten seaweed, and something akin to the essence of death itself. These odiferous occasions called for a stiff upper lip, but I wanted to spend as much time with my grandfather as I could because I also wanted to nurture my fascination with sailboats.

When I was with him, I watched the sailboats tie up and set sail from the pier. Still, I viewed sailing as I did tightrope walking and lion-taming. Sure, these all were awesome pursuits, but I had no desire to walk the high wire, work with a hungry lion – or step aboard a tippy boat propelled by the wind.

Some 20 years later, I was invited by friends to join them and their son on a cruise around Rockport Harbor on their 19-foot O’Day sailboat. They were wonderful friends, and I did not want to disappoint them, or embarrass myself by showing concern about the tippy nature of sailboats. So I accepted their invitation, packed sunblock, towels and snacks, and joined them at the pier. In hindsight, I probably should have inquired about how they liked to sail.

As I soon found out, they loved to bury the rail in the water, appearing to do their best to capsize the boat. I hung on with white knuckles and a forced smile, assuring them that I was having a great time, too.

My salvation came in the form of a summer thunderstorm rapidly rolling toward us. I expressed my Oscar-worthy regret that we were starting the engine, dropping the sails, and returning to port. And, despite the fear I had felt, the experience remained quite beautiful in my memory. I didn’t step on a sailboat again for another 15 years, during which time I learned to love powerboating.

With two friends, I had purchased a small motorboat with a little cabin and an engine that seemed to spend more time in the repair shop than on the boat. When we were able to be out on the ocean, we spent many days at Bassetts Island, in Pocasset Harbor, and in Buzzards Bay. I loved the speed of a powerboat. I also appreciated the many locations you could visit and still have plenty of time left to enjoy some beach time. I saw no reason to consider sailing when powerboating provided everything I thought I loved about being on the ocean.

In later years, when I met Red Poirier [see “Boats, Bass – and Beyond,” August 2014], we spent every possible waking hour on the ocean. When we weren’t actually on a boat, we were packing bags for an overnight cruise to the Vineyard or plotting a course for a new fishing spot. He embraced the ocean the way that I had my entire life. We were avid powerboaters for many years. I loved riding over the waves at a high speed and listening to the sound of the propeller as it came out of the water.

So imagine my surprise and curiosity when I began to notice that Red had become more knowledgeable about sailboats. When we were in the harbor, he had started to cruise around the mooring field, checking out the sailboats looking for the name of builders, hull designs, keel types and the like. Change was in the air, along with a fair measure of anxiety.

When the sailing magazines started to fill the coffee table, I knew that soon I might be giving sailing another chance. I decided to be open-minded and enthusiastic about buying a sailboat. The for-sale sign went up for our 20-foot Maritime Skiff, and the search for a sailboat was on.

We covered every boatyard, marina and private sale in eastern Massachusetts and Rhode Island, looking for just the right sailboat. Red scoured every newspaper and boating publication he could find. Then, one day, the phone in my office rang with his good news that he had found a Cal 22 sailboat for a reasonable price at a dealership in Marion, Mass. She was named the Cannoli, I could only hope that she had a low tipping nature, or whatever the correct sailboat term was.

The race to try his hand at sailing had begun, and Red could not get the Cannoli in the water fast enough. The fact that we knew little about sails, rigging, or anything else related to sailing, would not stop us. I liked to think of the Cannoli as the Holy Cannoli because, with the religious connotation, perhaps she would be kind to two novice sailors. Thinking ahead, I also thought that it was a better expletive to use than many others. Expletives were inevitable when learning to sail.

We secured a mooring at Kingman Marina, in Cataumet, Mass., and the Cannoli was delivered at the first available date. The boom and the sails were in the cabin. The first order of the day was to attach the boom to the mast, which seemed easy enough. It was certainly easy enough for me since Red was doing all of the work as I stood by, walking gingerly around the boat and hoping that it would not move with every step.

With the boom attached, and now contemplating the next step, it was clear that it was time for lunch, the Red Sox game on the radio, and a nap. So far, I was really beginning to like sailing. We were now ready to think about the sails, but it was time for coffee and dessert. We decided that our next day on the boat would be the day that we installed the sails. This required lots of planning and reading. I was content with the “Boston Sunday Globe,” but Red was bookmarking and highlighting boating magazine articles. The Cannoli was definitely in good hands.

Having rigged the sails, we were ready for our first sea trial. It was a very short trip. Red had figured out some of the basic sailing techniques, and I had flashbacks to the Norman’s Woe rock, off Gloucester, the site of Longfellow’s story of the daughter of a wrecked ship’s captain being lashed to the mast and perishing in a storm. That aside, I was impressed that he had learned so much in so short a time. There may have been a few “Holy Cannolis” uttered, and a few tense moments, as we tried to pick up the mooring ball. But, all in all, it was a good first day on the Cannoli.

Though we had done reasonably well on our first outing, we thought we could improve our skills if we hired someone to check the rigging and give us a few pointers. Red found an ad in the local paper for a sailing instructor who would teach new sailors on their own boats at a reasonable cost. We scheduled a lesson.

The Cal 22 is clearly intended for two, maybe three, average-sized souls. Two was better, and three was a bit of a stretch, but we thought we could accommodate the third person by leaving extra items ashore. Much to our dismay, the instructor, a large man, had brought along his girlfriend.

Apparently, his ad to teach you to sail on your own boat was shorthand for, “I don’t have a sailboat of my own, but I am reasonably sure that you will give me money to take you out on your boat, and I can bring my girlfriend on a cheap date to impress her with my skills at your expense.” We should have cancelled when we realized his actual agenda, but in our excitement about sailing, we gave him the benefit of the doubt. After he adjusted the sails, we untied the boat, and he promptly ran the Cannoli aground. So much for giving him the benefit of the doubt.

Eventually, we were able to get out of the muck and on our way – again. Throughout the four-hour trip, or four-hour ordeal, our “instructor” showed us nothing we had not already learned and done, except running aground. After that experience, we got out on the water as often as possible, in a variety of conditions, learning as much as we could about our new passion.

Since we generally sailed in the same area, we had developed some routines. It was our practice to drop the sails near Bassetts Island to facilitate maneuvering through the mooring field while looking for our mooring ball. Shortly after our ill-fated lesson, we were headed home when our engine started to sputter off Wings Neck. The engine continued to run for a short time, but it finally stopped running altogether.

The current was running fast, boat traffic was heavy, the wind was erratic, and we were new to sailing. All told, the prognosis was not favorable. This was a classic moment when you decide you must make lemonade out of lemons, or resort to calling the Grim Reaper for a tow. We opted to sail into the mooring field. We learned a lot about tacking that day, and we learned a great deal about tenacity. With little fanfare, but with great satisfaction, we arrived at our mooring and picked up the ball on the first try. And we never ran aground.

We spent many days practicing in familiar waters. It was enjoyable, but there was still a sense that we needed some additional guidance. Red asked a good friend with years of sailing experience if he would give us some tips aboard the Cannoli. He was agreeable, and Red picked him up at Kingman Yacht Center. He came aboard and helped us iron out some of the rough spots, and he encouraged us to continue learning by doing. His advice was what we needed to raise our confidence enough to enjoy sailing.

Thereafter, our sailing experience was often a symphony of silence, interrupted only by the cry of seagulls, or the sounds of the sails and the stays. The sky seemed a bluer blue, with little white clouds looking as if they had been painted with an artist’s brush. Strange how so much of this had gone unnoticed by me when we were powerboating. The summer went by quickly, and every time we went out sailing, I discovered something new that made me realize that sailing offered a new perspective to the world around me.

Some of our best sailing was in the fall. The seasonal boaters had returned home in large droves, and the mooring fields were wide open. The foliage along the shore was at its peak, and we were treated to a stunning array of vibrant red, russet and yellow leaves surrounded by evergreens. Soon, it was Indian Summer, and we wished it would go on forever. But the days were growing shorter, and we put the Cannoli away for the winter . . . but not before listening to a post-season Red Sox game, enjoying a great lunch, and savoring a bit of a nap onboard.

A semi-retired attorney, when not sailing her latest boat, a 22-foot O’Day out of Barden’s Boatyard in Sippican Harbor, Tricia McGrath, from Essex, Mass., enjoys traveling in the United States and, occasionally, in Europe; spending time with her family; writing a book; and keeping her hand in the practice of law. For those unfamiliar with Italian delicacies, cannolis are pastries that originated on the island of Sicily. They are tube-shaped shells of fried pastry dough, filled with a sweet, creamy filling, usually containing ricotta. Sweet!