Ready Or Not, Sailing Billy Pilgrim South

We couldn't know what unexpected themes would emerge until we did the unimaginable– untied our lines and set off.

Tim in NYC
Tim Murphy takes the helm with the Staten Island Ferry off to starboard. Tim Murphy

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Lesley and I weren’t ready for launch season. The ­projects we’d started in March to upgrade Billy Pilgrim, our 1988 Passport 40, still weren’t finished on June 1. New plumbing for the head. New electric winch in the cockpit. New ­navigation instruments. New 12-volt charging system. We weren’t ready when shakedown season came. 

We’d aimed to spend August sailing Maine’s Casco and Penobscot bays, learning our new gear and breaking what we could break before we left New England waters. But the mid-July discovery of a hand-me-down roller furler inspired an entirely unforeseen boatyard project at Portland’s Maine Yacht Center: adapting our hank-on staysail to one we could set and douse from the cockpit. Sundry other one-last-things stretched our launch all the way out to Labor Day. The first cold northeasterlies ­blasted us in late September 2021. We weren’t ready then either. 

But we could grow old waiting till we were ready, we figured, and maybe we already had. Dozens of projects stared back at us from the jumbled cabin full of equipment boxes and parts containers as we cast off our lines. Ready or not, it was time to go sailing.

Long Island Sound
Ready or not, Billy Pilgrim heads south, seen here taking advantage of a fresh north wind on Long Island Sound. Tim Murphy

Gloucester Harbor is its own pre-dawn alarm. We had set ours, but we clearly didn’t need to.

The voice came from inside, or seemed to, till we woke enough to notice the low diesel rumble outside our hull. The fisherman’s rage at some fellow crewmember or the skipper of a competing boat was loud. There were four souls tucked into Billy Pilgrim’s berths. We’d already provisioned the boat and slept aboard to get an early jump on the new day. Now, here, well before the sunrise, all of us were manifestly awake.

My parents, Tom and Sue Murphy, had joined Lesley and me for the first leg of a season-long passage down the US East Coast and beyond. Our destination was Somewhere South. When I was a young teenager, circa 1980, my folks had moved our family aboard a 41-foot ketch in Louisiana, and we spent six years cruising the Gulf Coast and Bahamas, years that indelibly formed each of us. 

For my dad, those years marked a transition from O’Hare air-traffic controller to yacht broker. He delivered boats—power and sail—numbering in the hundreds, and nearly all of them on fixed schedules. For him, these northern waters—the Gulf of Maine, Massachusetts and Buzzards bays, and Block Island Sound—had supplied a bottomless well of epic tales beset with zero-viz fog, steep breaking seas, icy speed-killing headwinds, foul tides and fouler fuel tanks. 

Billy Pilgrim
Checking out Billy Pilgrim’s roller-furling staysail at sunrise. Tim Murphy

More broadly, these waters meant something different to him than they did to us. One of my hopes for our trip together was to show my dad the idyllic New England playground Lesley and I had been enjoying for so many sweet seasons, sailing in conditions we chose. From the outset, it established a theme for Billy Pilgrim’s entire southbound season. We would never sail in bad weather.

My folks arrived on a Wednesday, duffel bags stuffed with the wool sweaters, foul-weather gear and inflatable life harnesses. They’d landed at Boston Logan International Airport ready to sail. We let Thursday pass, and Friday too, days of stiff southerlies blowing straight at us from the Cape Cod Canal’s eastern entrance. Instead, we sailed on a Saturday morning of light easterlies that required a diesel boost, but that landed us in the canal midday at full ebb, shooting us under the Bourne Bridge and past the Massachusetts Maritime Academy at 12 knots and more. 

I’d initially reckoned that we could make 60 miles in our available autumnal daylight and that we might end our first day in Onset or maybe Mattapoisett; as it happened, we made 87 and picked up a Cuttyhunk mooring with light still left to spare.

No shakedown was ever easy, and neither was ours. At the end of our first long day, too much water in the sump and too little water in the taps sent me chasing after leaks and bilge-pump fuses and blocked vents. The 20-year-old radar and chart-plotter display that had worked in 2018 now failed to power up; our temporary partial answer was an iPad in a zip-top bag, duct-taped to the binnacle—a solution we called our “redneck MFD.” And the beautiful Bimini that Lesley had painstakingly designed and sewn over several weeks when the rig was down now conflicted with the boom when the rig was up.

Still, the new Lavac toilet was working as advertised, and the NMEA 2000 backbone was magically sending electronic data between our new Vesper Cortex AIS and Raymarine wind and speed instruments. The Seldén E40i-powered winch on the cabin top made raising the mainsail from the cockpit a breeze, and the roller-furling staysail was a dream: a headsail that, when short-tacking or motorsailing, we could carry 20 degrees higher in the apparent wind than our big, drafty, 120 percent genoa.

Gloucester Harbor,
Preparing for an early departure from Gloucester Harbor, Massachusetts. Tim Murphy

That staysail demonstrated its worth on our second day out. Lesley and I each have daughters in New York City experiencing their first year in the workforce. If we wanted to see them, we’d have to land in the city near a Saturday. Cuttyhunk to Throg’s Neck is 140 westbound miles; averaging 5 knots down the rhumb line, that’d be three full daysailing days. Seemed fine on that September Sunday morning until we factored the forecast: at least three days of stiff westerlies. 

So, out came the staysail and up went the main, and for a few hours in a breeze that blew from north of west, we made good time toward Block Island in a boat that felt mighty fine. But as the sun climbed, the wind backed and built. Now, we were pointing toward somewhere east of Montauk, New York. As the seas steepened, 6 knots of boatspeed became 5, became 4, became… 

“Let’s tack.”

Now on port, we eased sheets, rolled out the genoa, and raced toward Newport, Rhode Island, my home for 30 years, on a glorious reach at 7-plus knots. It was only bad weather if we tried to sail west.

The address is tattooed on my soul: 524 Thames Street. It was the original home of Cruising World magazine, founded in Newport in 1974 by Australian Murray Davis. My parents subscribed all through the years they were transitioning from our suburban home in Chicagoland to our Taiwan ketch in a Louisiana bayou. For my part, after reading Robin Lee Graham’s Dove at age 10, I came to devour every monthly issue as it arrived. 

Cruising World’s authors—the Hiscocks, the Pardeys, Sven Lundin, Bruce Bingham, Betsy Holman, Danny Greene, Dan Spurr—were my heroes. I was a high school sophomore when I read a feature about the 130-foot brigantine Young America and answered a call in a sidebar for a scholarship from the American Sail Training Association. Only after I’d won it did I tell my parents I’d written the letter. By then, we were living aboard. 

To their everlasting credit, my folks packed up the boat’s galley (a portable Coleman cooler and camp stove plus propane bottle), built beds for my sister and me in the back of our GMC Jimmy, and made a monthlong adventure out of it. We arrived in Newport one day ahead of the 1982 Parade of Sail that would commence my weeklong sail-training cruise, and we set up camp right downtown on Long Wharf where the Marriott now stands. When they asked what I wanted to do in Newport, I could think of only one thing.

Brooklyn Bridge
Cruising under the Brooklyn Bridge on New York’s East River. Tim Murphy

“Go to 524 Thames Street,” I said. Standing in front of it, I didn’t know what to do except gawk.

That was 40 years ago. I’d spent the next six months crewing on Young America, sailing as far as Key West, Florida, and then cruised the Bahamas with my parents. I finished high school, earned a 100-ton captain’s license, worked on boats, went to college, lived in Paris and Berlin, and came back home to study journalism. In 1991, Bernadette Bernon hired me as a Cruising World assistant editor, and all the strands of my life came together. 

All these memories came flooding in as Billy Pilgrim reached past Castle Hill, Rhode Island, under full sail, overtaking the schooners Aquidneck and Madeleine, and rounding Clingstone on the Jamestown side. I wanted to sail under the Newport Bridge in a victory lap that would follow the course of that 1982 Parade of Sail that was my first-ever look at Narragansett Bay. Yet the sun was lowering and reason prevailed. We furled sails and took a mooring from Oldport Marine. 

After three days on board, the hot ­showers at Newport Maritime Center—seven minutes for seven quarters—couldn’t have possibly felt better. And when my folks asked where we might go for dinner, the answer was easy: Zelda’s Cafe, founded by Murray Davis in the same building where he’d established Cruising World and the Seven Seas book press.

Our improvised tack on that Sunday afternoon changed the whole tenor of Billy Pilgrim’s cruise so far. For one thing, it took away the feeling of a forced march we’d imposed on ourselves. More important, it introduced a second theme: the way traveling by boat can deepen otherwise old and familiar relationships in wholly new ways.

Lesley Davison
Lesley Davison tackles a head project. Tim Murphy

As the wind on Monday still blew stiff from the west, we used it to take at least part of that Narragansett Bay victory cruise, beam-reaching up over the top of Jamestown with all sails set, then close-reaching into Wickford Harbor to visit Ed Sherman, my co-author for the high school textbook Fundamentals of Marine Service Technology (ABYC, 2012). When Tuesday’s breeze continued from the west, now with lines of severe thunderstorms, we stayed put in Wickford, using the day to reprovision and make chandlery runs, fixing at least some of the faults our initial shakedown had revealed.

Wednesday and Thursday were perfect days on Long Island Sound. A fresh, clear norther filled in. We left Wickford before dawn and power-reached past Point Judith, through the Race, and all along the Connecticut shoreline. With flat seas and a fair tide through most of both days, Billy P consistently logged speeds in the high 7s—better than hull speed for a 34-foot waterline. 

On Wednesday, as we neared the Thimble Islands toward sunset, I texted Doug Logan, author of BoatSense (Seapoint Books, 2019) and an old mate from my Cruising World days who lives in that neighborhood. Logan zipped out in his Boston Whaler and led us into a lovely, marginally marked hidey-hole that’s nicely tucked away out of current. We caught up as though no time had passed. Before sunset Thursday, we picked up a City Island Yacht Club mooring in New York, our next big mission accomplished.

“Can I come see you tonight?” my daughter Kate texted. She was still in her classroom where she teaches in the Bronx, a short distance from City Island—so near, yet so far.

“Code switch!” Kate shouted as she stepped out of the dinghy and into Billy Pilgrim’s cockpit. In truth, I barely recognized the poised and elegant young woman arriving from work in the inner city. She and her grandparents enjoyed an evening together while I chased clogs in the shower sump and Lesley composed a meal from galley scraps.

At City Island, my parents left Billy Pilgrim—but not the same as they’d arrived. For them, our week together rekindled old memories and reignited a new search for a boat of their own. For all of us, revisiting those old memories and making new ones was a gift we’ll carry forever.

Meanwhile, Lesley and I transitioned from intense encounters with my parents to intense encounters with our children. Lesley’s cousin, Scott Perrin, invited us and the girls for a Saturday cruise of the East and Hudson rivers aboard Great Scott, his Stevens 70 motoryacht. Riker’s Island, the UN Building, the Brooklyn Bridge, the new Little Island complex and, of course, the Statue of Liberty—there’s simply nothing like seeing New York City from the water. 

On Sunday, Lesley and I went our separate ways for one-on-one check-ins with our respective kids as they navigated some of the first major transitions of their adult lives. Late Sunday night, we returned to Billy P to get ourselves ready for our next mission.

Like riding a horse with four legs of different lengths” is how Lesley described Billy Pilgrim’smotion as we made our way out New York Harbor and into the Atlantic Ocean. For the first time in years, we were underway aboard Billy P and alone on the ocean, just the two of us. Most of Lesley’s lifetime sailing experience had been with me, and since 2018, that amounted to exactly zero. 

We reckoned we lacked sufficient daylight to make it from Sandy Hook, New Jersey, to Atlantic City, the first good inlet on the Jersey coast. Rather than enter a strange inlet in the dark, we decided to leave New York Harbor at noon, run outside overnight, and enter Delaware Bay shortly after dawn the next morning. And so, into a gentle breeze from the east-southeast, we motorsailed with full main and staysail. We passed Shrewsbury and Asbury Park, and as the light began to wane, Lesley blasted Bruce Springsteen from a portable speaker in the cockpit to keep her spirits up. Still, her courage faltered as the sun went down.

“I’m not prepared for this,” she said.

And she wasn’t wrong. For all my previous experience, I was rusty too. We were suited up in our harnesses and tethers, with jacklines run forward. As commercial ships passed to seaward of us, we rehearsed right-of-way rules and the patterns of running lights till they started to blur.

“White over white, towing at night.”

“White over red, pilot ahead.”

“Red over yellow, have you never been mellow?”

I went below for a two-hour nap, then came back on while Lesley slept. To the east, a strangely lit vessel was moving erratically. Blue lights, green lights, red lights, white lights. I watched its relative bearing for a while, unable to tell how far away it was. I missed our radar. Eventually, the vessel moved to the left and disappeared over the horizon, with no course or speed change from me.

The next set of lights disturbed me even more. This one was to starboard, inshore, and it first appeared as a bright white light with a glowing loom around it. Then, a red light would appear. As it was to starboard and showing its red sidelight, that made me the give-way vessel. But the red light would disappear, and then the white light too. Then they’d return. 

I tried slowing down, but the relative bearing of the light cluster remained nearly constant. I tried altering course 10, 20, 30 degrees to port. After 20 minutes, other lights appeared around it. Finally, it dawned on me: The vessel I was trying so hard not to collide with was Atlantic City, some 20 miles away. 

Now, I really missed our radar.

Since then, Lesley and I have stood ­many night watches up and down the coast. But none was weirder than that first night off Jersey Shore. 

On my next watch, I finally had time to study the Vesper manual and learn to read the AIS targets on the small handset. This proved a comfort as we approached the converging traffic at the Delaware Bay entrance. We rounded Cape May as the sun rose, and spent an easy day motorsailing toward the Chesapeake and Delaware Canal, just outside the main shipping channel, passing great ocean cargo ships at close range.

“The banks were low, the light was warm,” Lesley wrote of Delaware Bay. “It all seemed a bit like a Dutch landscape painting with an industrial twist.”

Dumb luck favored us with a fair current at the Cape Cod Canal and at the Race, so it favored us in the canal between the Delaware and Chesapeake bays. We entered the Chesapeake in late afternoon, and hustled to make the Sassafras River before nightfall.

New York harbor
There’s no view of Manhattan quite like the one from aboard your boat along New York Harbor. Tim Murphy

“It didn’t seem possible that the water we found ourselves in at the end of the day was the same element we’d been in off New Jersey,” Lesley wrote on Billy Pilgrim’s blog. “This was as soft and smooth and gentle as the previous water had been pointy and lively.” 

We dropped the anchor and together made a spectacular decision: We wouldn’t cook.

We instead had beer for dinner.

Lesley and I woke next morning to the realization that we’d accomplished our biggest mission yet. We’d sailed out of fall and back into summer. First thing, before breakfast, we dived over the side and swam in water that was comfortably warm and almost entirely unsalted.

If Narragansett Bay was a victory lap, then our arrival in the Chesapeake Bay was something still grander. We made our way to the Severn River and dropped anchor off the seawall of the United States Naval Academy on the eve of the United States Powerboat Show. It was a scene of delightful mayhem. On our way in, we passed the 160-foot three-masted ­schooner Arabella, anchored nearby. Before I’d secured the snubber on our anchor rode, a text came through my phone from Melanie Neale in St. Augustine, a friend in Florida: a real-time photo of Billy Pilgrim in that Annapolis, Maryland, anchorage. Turns out, the photo had been shot by our mutual friend Tom Thompson, Arabella’s captain. We barely had the dinghy off the davits when a text came through from him. 

“Come have dinner with us,” he said. “Our Peruvian chef is cooking.”

Those first beers on the Sassafras tasted good, but the ones we toasted with on Arabella tasted better still. For the next couple of weeks, the social flurry would outclass even the one we’d experienced in New York. Through it all, in our hearts, Lesley and I carried something fine. We’d done the unimaginable. We’d untied the lines.

We’d set off.

Tim Murphy, a Cruising World editor-­at-large and a longtime Boat of the Year judge, is the author of Adventurous Use of the Sea: Formidable Stories of a Century of Sailing from the Cruising Club of America (Seapoint Books, fall 2022). To read Lesley Davison’s version of Billy Pilgrim’s 2021-22 southbound season, visit

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