My own sailing legacy

By Shirley Cassara
For Points East

The author and her husband, Marc, aboard Windigo II, their Sabre 30 Mark III. Photo courtesy Shirley Cassara

Our friends and family had braved the dirt roads of western Maine to attend our wedding. It took place in sunshine and gentle breezes, on the side of a foothill of the White Mountains.

It all went to plan, much to the surprise of the doubters, who, after days of rain, had not held out much hope. A jolly time was had by all, although elderly relatives made their excuses early, to navigate their way back to civilization before darkness fell.

So what do sailors do for a honeymoon? They hightail it to the coast, of course. Our home base was to be my husband Marc’s family retreat in Southwest Harbor, and our plan was to charter a boat so my beau could sail me to his favorite haunts from childhood.

We had one week in which to soak up enough glorious sailing to carry us through the winter, but each morning we stepped out into a world thick-o-fog. We pretended to each other that we didn’t mind; after all, we had lobster to eat, heron to seek out and photograph (if we could find them in the mist), damp hikes to take, and tea and popovers with which to console ourselves.

We stuck our toes in the water at Acadia’s Sand Beach, and watched the fog drift back and forth while we quoted poet Carl Sandburg. We had one of our famous picnics by the lighthouse in Bass Harbor – at least we think that was where we were. It must have been a sign that our luck was going to change when a bird perched on my head as we sat in Asticou Gardens in Seal Harbor.

When buying provisions for our picnics and grill, we had been scouring the bulletin boards and local newspaper for boats we could charter. We had to hope, after all. Thursday morning broke bright and clear, with light air, and my hero found a phone number he had pocketed, reserving a Luders 16 for the day. I madly packed lunch, the dog and our foulies, and we went in search of our boat.

We expected a long, drawn-out set of cautions and concerns, and maybe a contract to sign, but the woman of the house simply handed us the companionway key and told us the launch driver would take us to the boat. The last thing she said, as she shooed us out the door, was to put the key and a check through the letter slot at day’s end.

The winds were light as we sailed out of Northeast Harbor and along the Eastern Way. When they petered out, we were off The Bubbles mountains and in warm afternoon sunshine, and I was lulled to sleep by the lapping of the waves on the hull. Suddenly, my new skipper broke the reverie, telling me the wind was up and we had better get under way if we were to return by sunset.

The wind freshened, and our foulies dripped with the spray cascading over us. When the lee rail went under, the picnic cooler shot out from under us and hit the dog, who was sheltering under the leeward bench. She bolted for the cuddy cabin, not to be seen again for the duration.

At this point, I wondered if I should be scared, but when I peeked out from around my hood, my partner was the model of composure, with a decided tinge of pleasure thrown in for good measure.

Just as I was thinking we were doing the Luders’ owners proud, there was an almighty CRACK. A fissure appeared in my partner’s composure, too. It isn’t polite to pop fairleads off other people’s boats, even when you were showing their boat to its best advantage. Lucky for us, the owners acted as if this were par for the course.

We gained the harbor, and, having no motor, we sailed onto the mooring in fine form, retrieved the quivering dog from her cave, and congratulated ourselves that, fog be-damned, we had packed a whole week of sailing into one day. The bottle of champagne my father had sent with us on our honeymoon didn’t last long.

I learned a lot from that day: Being a sailor organizes a person’s thought-processes in a special way, a characteristic I wanted to share. But I didn’t realize then that speed in sailing was to be the cornerstone of my husband’s passion.

Sailing has proven to be the reliable foundation of our marriage. It requires mindfulness and problem-solving, reliability in tough situations, and an insatiable thirst for adventure. One of the more flattering compliments my husband has relayed to others is that I am the one person he wants to be with when the going gets tough – literally and metaphorically.

One of my favorite photos, taken a few years later, is of our son, Travis, at 4, peering around the stanchions of our first boat, a trailerable Sirius 21. Having been practically born afloat, he was comfortable in boats and showed a rowing expertise from before he could walk. He came to expect that he would have to move from his bunk in this tiny floating universe when it was time for me to light the alcohol stove, near his head, and reach under his bunk for the cereal.

A few years later, when his sister Susannah arrived, he took great pride in indoctrinating her to the sailing life. As she was turning 1, we joined English friends for another trip of a lifetime. We chartered a 50-foot motor cruiser on the Norfolk Broads, a network of lakes and rivers in England. This was not only an out-of-our-ordinary adventure, but it also brought to life the “Swallows and Amazons” books by Arthur Ransome, to which I was introduced while living in England as a child. In this case, it was the escapades and environmental activism of a band of youngsters on the Broads, the “Death and Glories,” in the book “Coot Club.”

The Norfolk Broads present challenges most of us on the East Coast could never imagine: Tidal rivers are not in flood at the same time, and one must know how to navigate them. If you get the timing wrong, you end up high and dry: Where you thought there would be a lake, there would be expansive acreage of mud with a trickle down the middle.

It was glorious to discover the settings in which Ransome placed the children’s exploits. Though Susannah was very young on this cruise, she incorporated these stories into the narrative of her life, too, as we continued to read them to the kids at bedtime as they grew.

Of course, we outgrew the Sirius pretty quickly, but before we could decide on another vessel, we were invited to accompany some sailing friends on a Caribbean journey, which was another waypoint for the family. Sailing on one tack, down the length of the Windward Islands, was breathtaking, enhanced, of course, by the stops at such natural wonders as Tobago Cay.

Once again, the family’s body of experiences was enriched. We were assigned a remarkable charter captain, who took our 8-year-old son under his wing, and had him doing everything along with him. The fathers showed occasional jealousy at the amount of time he spent at the helm.

Our daughter found her sea legs on her second birthday, celebrated on board. By the time we stepped off of our vessel in Granada, after 10 days, she could no longer walk on a dock or land without a helping hand – like any old salt disembarking after a long voyage. Ten days of sailing in the Caribbean also gave us the seascape with which to visualize Arthur Ransome’s “Peter Duck,” the tale of Swallows and Amazons kids sailing from Lowestoft, England, to fictitious Crab Island, off the coast of South America, in a small schooner named Wild Cat.

After much research and consideration, we moved up to a Garry Hoyt-designed Freedom 32, which, for me, was an ideal boat as it was family friendly and conducive to my gaining confidence at the helm. This boat was so important in our children’s lives that they shed many tears when it was time to sell.

So, what does a sailing family do while they are in search of the next prize? Well, my husband became a yacht broker; all the better to have the inside scoop of what was coming on the market. At the same time, my son went to sailing camp and raced 420s at Massachusetts Maritime Academy for several summers.

Not to be outdone, our daughter undertook the obligatory Opti training camp, and we bought her a small Walker Bay for her to skipper and me to crew. We joined the regatta committee, racing Capris at our club on Tuesday nights, which gave the kids and me the experience of the racing edge of which my husband often spoke.

You never know the influence these adventures – and the culture of the high seas – might have. Fast-forward to his college years, and our son branched out into tall ships, doing a semester at sea aboard the Spirit of Massachusetts, a 3,500-mile journey around the Caribbean and up the East Coast. His sister was taking notes. She acquired a poster of the schooner Bowdoin at the Maine Boatbuilders Show, and put it on her bedroom wall. She quietly set her sights on attending Maine Maritime Academy, all other colleges be damned, because they did not have a tall ship for her to cut her teeth on.

In fact, she graduated with the dual degree in Marine Science and Vessel Operations, and was Student Chief Mate of the Bowdoin in her junior and senior years. She graduated with her 200-ton Mate’s license, and, as I write, she is sitting the exam for her 100-ton Master’s. In her work, she has sailed many kinds of vessels, large and small, and she always acquaints me with them with references to a similar craft in Ransome’s stories.

In time, my husband owned up to an ardent desire to be able to sail fast. So, after too many boatless years, a Sabre 30 Mark III came on the market and we dived on it. His passion, above all else, is tuning and fine-tuning, refurbishing and refitting. So now, as we steal around Salem Sound, on Massachusetts’ North Shore, we often outpace large yachts, while disconcerted skippers give us the side eye. Our son, meanwhile, is breaking his wife into the wonderful world of sailing.

My husband? My skipper figures that we need to get a larger vessel – as long as it sails fast – so our growing family will join us for the next set of adventures. He is deep into a search for the next seagoing boat that meets his criteria.

How did Arthur Ransome conceive of confidence-building in girls and boys through sailing story telling? I wish I knew. While my husband’s legacy evolved from being born with a winch handle for a rattle, mine has grown from Arthur Ransome’s stories and my own experiences. So I will have to content myself with infusing the magic and timelessness of “Swallows and Amazons” into the sailing experiences I share with today’s children. Hopefully, the love of a good nautical adventure will inspire the next generation to fall in love with the oceans and waterways – and to revel in messing around in boats.

When not out on the water, or performing spring commissioning, or writing, or organizing the NWSA Women’s Sailing Conference, Shirley Cassara is a semi-retired college professor of child psychology. Her accumulated enthusiasm for learning and adventure on boats has allowed her to enjoy sailing and crewing on dinghies up to tall ships. At the moment, however, most of her time is spent trying to bury the rail in Salem Sound with her husband on their Sabre 30 Mark III.