It was in my late teens, racing as crew on a small offshore sailboat in the middle of a cold, foggy English Channel, that I had my saltwater epiphany. I’ll never know where it came from or why it chose that moment, but it struck with an impact that I remember clearly to this day. It felt like a release of some kind: I had finally come home and was where I belonged. That feeling has never left me.

I learned to prefer heavy-weather sailing because the boat moved faster, and I enjoyed the challenges it presented. But above all, I loved being far away from land in an ever-changing ocean. There was a feeling of lonely independence, and the self-reliance it engendered. I covered a lot of ground, won some races, ran some charters in the Caribbean, and delivered numerous boats from the Caribbean through New England and most places in between.

The beautifully rugged coastline of Long Island Sound offers prime gunkholing opportunities for inquisitive mariners. 

The beautifully rugged coastline of Long Island Sound offers prime gunkholing opportunities for inquisitive mariners. 

But I never really experienced the unique joys of cruising until I spent 10 years in New England, bought a sailboat, and began to explore Long Island Sound and beyond. It was a second epiphany. How lucky can you get?

The thing about cruising in New England is the seemingly unlimited number of places to drop anchor (or pick up a mooring buoy), kick back and allow time for nature to sink into your soul. From where I kept my boat in Connecticut’s Niantic River, it was a mere five minutes to a small, sandy beach that afforded good holding ground and a plentiful supply of clams (chilled white wine was compliments of the boat’s provisions).

Originally constructed in 1746, Nantucket’s Brant Point Lighthouse ranks among the region’s most iconic maritime treasures. 

Originally constructed in 1746, Nantucket’s Brant Point Lighthouse ranks among the region’s most iconic maritime treasures. 

But beyond that, on any given day, we could cruise in almost any direction and find a nice spot whenever we felt like stopping, from 30 minutes to, well, as long as we felt like sailing. Hamburg Cove, Coecles Harbor, Dering Harbor, Sag Harbor, Shelter Island, Essex, Peconic Bay, Block Island—more than a few stick in the memory, but the list doesn’t include the hundreds of small coves, creeks and estuaries that afford convenient and delightful anchorages on any given day.

And, New England offers cruising features for those of us who still enjoy a little challenge in our passagemaking lives.

The idea for one such cruise had been planted on a cold, mid-January evening in Connecticut, over pizzas and a jug of Chianti at the local place where I and two good sailing buddies liked to huddle in the winter.

“How about a two-boat cruise, with our three boys taking one of the boats and us another, and spend a week cruising?”

The idea was instantly adopted and discussed, and a round-trip itinerary from Niantic to Nantucket was chosen. The boys were consulted and immediately agreed (a remarkable event for three high-school freshmen).

Northern exposure.  Originally located on an artificial island a quarter mile from shore, Edgartown Harbor Light on Martha’s Vineyard is now surrounded by a beach formed by sand accumulating around the stone causeway that connects it to the mainland.

Northern exposure. Originally located on an artificial island a quarter mile from shore, Edgartown Harbor Light on Martha’s Vineyard is now surrounded by a beach formed by sand accumulating around the stone causeway that connects it to the mainland.

We left at night on a warm June evening and arrived the following morning at Cuttyhunk Island, where we anchored and rafted up at the edge of the main channel. A front had moved through during the night and left in its wake a steady 35-knot breeze, with higher gusts and a chill that demanded heavy sweaters and hot beverages.

Deciding to move on, we left Cuttyhunk with double-reefed mainsails and enjoyed a bumpy ride around the south of the island, where we set a northeasterly course to take us through Vineyard Sound and, from there, into Nantucket Sound and our destination, Nantucket Island. The wind moderated during the day, and by the time we reached Nantucket Sound, we were enjoying a comfortable ride in warm sunshine. Life was good.

We arrived at the narrow entrance channel in Nantucket at exactly the same time as the Nantucket Ferry, requiring us to hug the edge of the channel to allow it to pass. Once we were inside and safely rafted to a mooring in the picturesque harbor, we spent two delightful days relaxing, drying wet sailing clothes, taking on fuel and provisions, exploring the historic island (home of, among others, Herman Melville’s fictional characters from Moby-Dick) and, of course, helping to reduce the local lobster population.

Nantucket fog. Some say that the most difficult thing about navigating Nantucket is finding an open mooring. Our crew found its fog to be a bit more challenging.

Nantucket fog. Some say that the most difficult thing about navigating Nantucket is finding an open mooring. Our crew found its fog to be a bit more challenging.

Then, we were off through Nantucket Shoals, an area of dangerously shallow water that extends from Nantucket Island eastward for 23 miles and southeastward for 40 miles. It’s the graveyard of many ships throughout history. The navigable channel from the sound is well marked but needs careful attention. We followed the boys as they cautiously picked their way through the channel to open ocean.

It was a perfect evening with enough wind to keep the boats moving well. We, for some reason, had Greek bouzouki music playing on the stereo as we relaxed in the cockpit watching a spectacular sunset and thinking about dinner.

That’s when a voice on the VHF radio announced: “We don’t seem to have any cold cuts on our boat. We think we left them all on yours by mistake, and need them for dinner.”

 Sub spotting. A chance submarine encounter just astern one of our boats was a sobering reminder that we never truly have the sea all to ourselves.

 Sub spotting. A chance submarine encounter just astern one of our boats was a sobering reminder that we never truly have the sea all to ourselves.

Ah, we thought, a good lesson in responsibility.

“The thing is,” came the reply, “We have all the beer on our boat.”

Point, counterpoint.

We agreed to bring the boats together to make a transfer—the first open-ocean transfer of cold cuts for beer in history, of which we were aware.

Our plan that night was for a 95-mile offshore hike, running south of Block Island to The Race at the western end of Fishers Island, a route that would bring us back into our home waters of Long Island Sound. After a picture-perfect evening, we established watches and settled in for a comfortable night passage.

It was not to be. Around 10 p.m., we were rudely reminded of Elin Hilderbrand’s classic description: “June and July are foggy months. In the early summer on Nantucket, warm, moist air flows over the colder water. The moist air cools to its dew point, and a cloud forms at the water’s surface. This is fog.”

Tones of home. Walls of lobster pot buoys conjure up cravings for the favorite local fare. Just mind your running gear when they’re in the water.

Tones of home. Walls of lobster pot buoys conjure up cravings for the favorite local fare. Just mind your running gear when they’re in the water.

This was, indeed, fog. The boats closed to within 50 feet of each other to maintain visual contact, and for the next 12 hours, with foghorns blasting, we motored through liquid air, drenched, keeping up our spirits with banter over the VHF radio.

Before noon the next morning, the sun had managed to burn off the fog as we entered Long Island Sound in high spirits and perfect weather, heading to our home port in Niantic. The boys were about half a mile ahead of us when we noticed an Ohio-class nuclear submarine about 100 yards behind them—not an unusual sight in these waters, since the U.S. Navy operates submarines from its base on the Thames River.

“Have you noticed the submarine on your tail?” we asked.

“Sure,” came the cocky reply. “Very funny.”

Ten seconds later, with a very different tone of voice, we heard, “Dad? What do we do about this submarine?”

We replied: “Suggest you hold your present course and speed, and monitor channel 16 on the VHF. If they need you to move, they’ll tell you.”

We could only imagine the white-knuckle tension on their boat as the hulking submarine bore down on them before safely passing by.

Immune to chain stores and neon lights, Nantucket’s Historic District is a picture-perfect place to hop off the boat and take in the area’s quaint ambience and rich maritime history. 

Immune to chain stores and neon lights, Nantucket’s Historic District is a picture-perfect place to hop off the boat and take in the area’s quaint ambience and rich maritime history. 

The following winter found my two sailing buddies and me again sharing pizzas. The conversation had turned to the Nantucket cruise with the boys, and the stories began to flow along with the laughter. What adventures! And on a deeper level, we understood that cruising itself ingrains experiences on a person that last a lifetime. At some time during these reflections, another jug of Chianti was ordered.

I’m still an offshore guy at heart; always will be. But the days are long gone when I can simply drop everything and take off on another adventure far from land and of uncertain duration. I feel blessed to have had those experiences, and miss them. But cruising, while sharing many of the same challenges, works in a different dimension, one that can be planned at a more leisurely pace. It allows for more social interaction, time for reflection and enjoyment of the environment, while at the same time requiring the same boat handling and navigation skills. We learn that a good life afloat is one we live to the fullest with friends and family. And that, surely, is what cruising is all about.

This feature originally appeared in the April 2020 issue of Passagemaker Magazine.

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