Isn’t it funny how things turn out? Go to a boat show, ostensibly to see the vessel your children are considering for themselves and you end up purchasing one yourself. After one boat show visit, a chain reaction of events gets set in motion, culminating in life-changing decisions.

We were at the Norwalk Show, September 2010, when we first laid eyes on her. We met our son to see what he was eyeing for his own family, and then let him steer us toward the Downeast Maine style, which he envisioned for his parents. He was anxious to see us return to the more classic, nautical look of our very first vessel. Jay was only seven years old at the time, but the image of his dad, seated at the helm of Diplomat I, our 1973 40-foot Pacemaker, smoking his pipe, will stay with him forever. Though both pipe and vessel are long since gone, the memories serve as a standard against which everything else is measured.

As you can imagine, in Jay’s eyes, the cruiser styled Diplomat II and Diplomat III that followed years later when he and his brothers were much older, simply did not cut it. While neither of these more recent vessels evoked any special nostalgia for our earlier boating days, my husband and I did have a lot of fun. With our 27-foot Maxim, George and I explored the waters around Long Island and Block Island. The Cruisers 34-foot Express that replaced her over the next ten years provided a bit more comfort. We extended our boundaries to Newport, the Vineyard, and Nantucket to the east, Red Bank, New Jersey to the west, and Catskill, on the Hudson, to the north. We’ve had no regrets, but as baby boomers, we wanted a vessel more sympathetic to us “older folks.” Like a parent redirecting his children to avoid a potential “mistake,” our son introduced us to and highlighted the benefits of the Downeaster. After some casual browsing, we settled at DiMillo Yacht Broker’s in-water display.

LOVE AT FIRST SIGHT

Before we knew it, we were hooked! Chris DiMillo made us feel comfortable right away. We looked at all the Back Coves and Sabres on display before we all came to the conclusion that the Back Cove 37 was for us. She certainly had the classic look and nautical charm that our last two boats lacked, and she also provided the upgrades we sought. As a woman, I responded immediately to the open layout, with the aft deck, saloon, helm station, and galley all in one roomy area. We could now cruise, relax, and entertain, almost as comfortably as at home. Imagine, my own navigator’s seat, next to the captain’s! Easy access to handle the lines, with wide walk-around sides, plenty of storage, and best of all, la piece de resistance, a second stateroom, for our grandchildren or other guests! I was getting excited. My husband quickly noted other benefits. The isinglass we both disliked was replaced with glass: wide glass doors that open the aft deck to the saloon, and wide glass windows that provide panoramic views, allowing sunlight to flood the interior. Oh, did I mention the air conditioning at the helm, an absolute “must” for George, and the fuel efficiency of the powerful, single engine? Although this last feature did present some concern, since he has always run (and still prefers) twin screws, the adjustment he’d have to make seemed like a small price to pay for an otherwise perfect package.

We left the show that afternoon more than just a little excited. Within a few short weeks we were out on Long Island Sound with Dave, our broker, to sea trial a demo. It was an ideal day to show off the vessel. Cruising at about 19 knots, she glided so effortlessly across the water, barely feeling the wakes of other boats. With George at the helm, I stood aft by the opened glass doors. Soaking in the sun on a glorious, lazy, autumn day, breathing in the fresh salty air with a gentle breeze stroking my face, I couldn’t imagine a better way to enjoy a perfect day. Before I realized it, I heard myself declare, “I think I’m falling in love.” A second sea trial a few weeks later in less perfect conditions only confirmed our feelings. Various maneuvers as the waves in the Sound began to build only proved once again how well she handled. When George quietly asked me if I’d like him to continue with serious discussions, the question seemed like a no-brainer.

A WINTER OF ANTICIPATION

Once we made the decision to purchase, the months ahead were, for me, like one long pregnancy. Having a vessel built for you is not at all like purchasing one ready to go. From conception to delivery, excitement and anticipation mounted daily as we prepared for our new arrival. With Diplomat IV under construction in Maine, we turned our attention to having her outfitted. Navigating our way through the maze of endless details that needed to be addressed turned out to be a process in and of itself. Walking the boat shows gave us a good exposure to the dizzying array of new products on the market.

The literature we lugged home to sift through later helped remind us what we didn’t want to forget. Everything imaginable was examined, as we kept an eye on expenses. George decided to go with Raymarine for his electronics. I hooked up with Susan August-Brown in Maine for the interior design. A second refrigerator was added to the galley. Bow and stern thruster options were reviewed. We purchased a life raft. Decisions regarding tenders and davit systems were left for another day. We had a long, busy winter, but it was all a labor of love.

MY LIFE-CHANGING DECISION

So what was my problem? Why, in the midst of all this anticipation, did my stomach start churning? After all the months of preparation, as we were about to be the proud owners of a vessel so perfect for us, why was I starting to feel uneasy? Considering the seaworthiness of our new acquisition, our horizons were suddenly expanding. No longer did we feel limited to local summer cruising, which dovetailed so well with my teaching career. Ah, there lay the rub. New ports of call were tempting, yet these new distant destinations required another big, very difficult decision for me to make. I’ve flirted with the idea of retiring before, always postponing it. In fact, my career has been so fulfilling and change isn’t easy for me. I’d miss the work, my sense of productivity, the camaraderie of my colleagues and, yes, the structure as well. The last time I made this decision was decades ago, when we became the proud parents of our first child. Was I ready for another life-changing event? Was I ready to take the plunge? As winter turned to spring, I wrestled with this decision; I loved working, but in reality Diplomat IV was not merely a vehicle to cruise familiar waters or even new waters. In my mind it became the very symbol of all the possibilities unfolding, which we’d be fools not to enjoy. I began to sense that perhaps the time had come to look ahead, to allow some doors to close while new ones open. Knowing that only a public statement would end my ambivalence, I finally marched myself into the principal’s office to announce my decision.

BRINGING HER HOME

That was several months ago. On Memorial Day weekend in 2011, with Dave aboard, we brought Diplomat IV home, delivering her from Glen Cove, New York on Long Island Sound, to Merrick on the south shore of Long Island. Though we like to think of ourselves as seasoned boaters, we approached our new purchase with the same care experienced parents bring to their newborn. After all, she was quite different from her three predecessors. The longer hull, newer systems, and single engine all took a little getting used to. We learned, quickly enough, that bow and stern thrusters, wonderful as they are for docking, do not always compensate for strong wind. We discovered that line caddies, installed at our home dock, make my job easier. The lines sit neatly in the caddies while we’re away, at a height level with the deck. When we return home, I can secure the lines without leaving the boat. Most interestingly, we tried out Eartec Simultalk full duplex radios. These hands-free devices come with headsets and allowed us to communicate calmly and civilly between the glass-enclosed helm and the foredeck, as we pulled out of one port and docked at another. They were handy as we practiced our boat handling, meandering out to the Hamptons and Greenport, New York, across the Sound to Old Saybrook, Connecticut, and Newport, Rhode Island, before heading home. They worked quite well, in fact, until we cast off from Maidstone Harbor Marina in East Hampton. I was pulling up a fender when my radio flew out of my pocket, leaving me helpless as I watched it arc wide before crashing into the water. To my embarrassment and George’s dismay, I felt like anything but a seasoned boater. Eager to improve my performance, as well as our basic knowledge and confidence as a cruising couple, you can imagine how excited we were to learn about PassageMaker’s Trawler Fest. We signed up for the whole package, with instruction, seminars, and demonstrations.

So here I am today, bridging many gaps. The disparity between career and retirement is immense, as I move from one schedule so consuming to another so free of obligations. The change-up from one vessel to another that is larger, more comfortable, and more seaworthy is thrilling, yet for me, still a bit daunting. Finally, as we widen our horizons from local, familiar waters to new, more distant destinations, the promise of new adventures and new opportunities hangs in the air, feeling more and more palpable. How could I not be excited, with all these possibilities unfolding? As for our son who got the ball rolling, he and his wife and son are enjoying their 2001 twin-screw 34-foot Legacy. We are now three generations of family, looking forward to hooking up on the water. I must say chapter two never looked so good!