Sailing South To The Islands Aboard Billy Pilgrim

Georgia Sea Islands and the Exuma Cays in the Bahamas highlight Billy Pilgrim's southbound season.

Ossabaw Island
The golden marshes around Ossabaw Island, Georgia, offer a placid ­anchorage and a spectacular sunset. Lesley Davison

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Just as we stepped through the rusted, wrought-iron gates of St. Simons, Georgia’s so-called Strangers Cemetery, from hot daylight into a shadowy overgrown world of Spanish moss that dangled from the twisting branches of live oaks and wafted over eroding gravestones, we were startled by a ding from Jenny’s phone. Its message sent a quick chill down her spine: You have arrived at your destination.

Perfect chance had brought us to this spooky and wonderful place, though the journey began simply enough. Many weeks earlier, we’d asked Lesley’s cousin Scott Perrin, a veteran of several annual Intracoastal Waterway migrations between New England and Florida, for his favorite barbecue joint along the route.

“Southern Soul,” Scott said without hesitating, “on St. Simons Island.”

So when our friend Jenny Gifford flew to Savannah, Georgia, to join Lesley and me aboard Billy Pilgrim in Georgia’s Sea Islands for her Thanksgiving holiday, we built our wanderings around a visit to Southern Soul. 

The Atlantic coast Sea Islands preserve constellations of ­microcultures spanning from the coastal Carolinas through northern Florida. Isolated within semipermeable borders, these communities are separated by swiftly moving tidal waters with such Muskogee and Creek names as Ogeechee, Wassaw, Ossabaw, Sapelo and Altamaha. Other rivers and sounds are named for European saints: Catherine, Simon, Andrew, Mary. Through this Lowcountry stretches a US National Heritage Area called the Gullah Geechee Cultural Heritage Corridor, recognizing the ­speakers of the only distinctly African Creole language in the United States. All fall we’d been looking forward to lingering a while among these islands. 

As Lesley and I sailed south from Annapolis, Maryland, we eased ourselves from a jangly initial shakedown mode into a more satisfying cruising mode. Aboard Billy Pilgrim, a sweet rhythm evolved as we alternated between bursts of overnight doublehanded passagemaking off the coast, then longer stretches of daylight runs through the inside waterways, where we’d anchor at night and spend time ashore. Our prior experience on the Jersey coast (see “Ready or Not, Sailing Billy Pilgrim South,” September) had shuffled our ongoing refit priorities, bumping new radar up to the top of the list. In our early fall migration from New England to the Chesapeake, we’d been thrilled to sail from sweater weather back into swimming weather. But when we paused long enough in Annapolis to install the new radar, winter overtook us again. Ice on the deck let us know when we’d dawdled too long.

So, on one of the first days in November, we bundled up and jumped on the back side of a fall cold front. With a clear three-day northwesterly gusting to 30 knots, we set the genoa and raced at hull speed over Chesapeake whitecaps with just two overnight stops, one on the Little Choptank River, the other in Deltaville, Virginia. Though the cold temperatures stayed with us as long as the front, we were excited to see other signs of our southbound progress. The Potomac River mouth, still some 60 miles inside Chesapeake Bay and straddling the Maryland-Virginia state line, gave us our first pelicans. The next morning, our first bottlenose porpoises joined us in Deltaville.

At Norfolk, we faced a navigational choice: sail out into the Atlantic Ocean to round Cape Hatteras offshore, or proceed inside the Intracoastal Waterway starting at mile zero? On the outside route, we reckoned that three days would take us to Charleston, South Carolina. By contrast, in the ICW, where shoaling and stumps rule out running at night, the same three days would get us only to Beaufort, North Carolina. As it happened, an offshore forecast with winds of gale and hurricane force for the next five days simplified our decision. Inside we went. 

St. Catherine’s Island
St. Catherine’s Island, privately owned for zoological research, is accessible below mean high water. Lesley Davison

Here, again, we were excited to see the proof of our southbound progress. As we moved through Virginia’s North Landing River, bald cypress trees replaced maples and beeches, and through the Carolinas, palmettos proliferated. Approaching Beaufort from the Neuse River, we met our first majestic shrimp boats. Later that night, we savored the season’s first shrimp and grits—but not before visiting the Royal James Cafe, one of the ICW’s finest pool halls (in a cash-only Budweiser and Tom Petty kind of way).

Sailing offshore from Beaufort in a brisk but dying westerly, we made Charleston in another day and a half, a total of seven from Norfolk. We might have shaved off a day or more, but when the ICW started reminding Lesley of too many I-95 transits between Massachusetts and Florida, we took an off-ramp at Albemarle Sound and poked up the Scuppernong River to Columbia, North Carolina, to celebrate her birthday.

At Charleston, finally, we felt we’d arrived in the South. We knew we could still experience chilly cold fronts, but they’d no longer bring certain snow and ice. We paused for a long weekend, availing ourselves of the city’s Holy Spokes bike-share program, pedaling between our Ashley River anchorage and Charleston’s South of Broad neighborhood, and enjoying the many delights of that charming city. Cruising friends Dave and Sandy Gillespie from the Tayana 42 Bel Canto introduced us to the Pour House on James Island, a live-music venue that would be my second home if I lived just a little closer.

As we moved on down the Stono, Edisto and Cooper rivers toward Georgia, the music of the place began to fill Billy Pilgrim’s saloon. We started with Ranky Tanky, a contemporary Sea Islands roots band featuring ecstatic horns and harmonies and an infectious bamboula beat. After they won the 2020 Grammy award for Best Regional Roots Music Album, trumpeter Charlton Singleton described the band’s Gullah influences to an interviewer: “It consists of a bunch of islands that stretch from right off the southern part of North Carolina in the Wilmington area, down the coast of South Carolina, down the coast of Georgia to the top of Florida. On these little islands you had descendants of former West African slaves. They maintained a lot of their customs, a lot of their beliefs, a lot of their ways of life. The way they cooked, the way they worshiped at the church, the way they entertained themselves, the way they spoke—they had a very unique language. And so in Ranky Tanky, we interpret a lot of those songs, a lot of those kids’ games. Now some examples of those songs would be songs that you’ve probably heard, like Kumbaya. When you see seagrass basket weavers, when you see little girls and boys playing patty-cake and they’re clapping on two and four, all of those things are uniquely Gullah.”

Ranky Tanky was our gateway backward through time to the music of Bessie Jones and the Georgia Sea Island Singers, based out of St. Simons Island. I’d first seen and heard them in footage from 1960s Newport Folk Festivals. Encouraged by anthropologist Zora Neale Hurston and folklorist Alan Lomax beginning in the 1950s, Bessie Jones and company brought Gullah music and games to audiences at Carnegie Hall, the Monterey Folk Festival, the Smithsonian Institution, and Jimmy Carter’s 1977 presidential inauguration.

In Thunderbolt, Georgia, near Savannah, Jenny Gifford joined us. With her, we ambled down the Skidaway River past the genteel porches of Isle of Hope and across the Moon River of Johnny Mercer fame. On some future passage through these islands, we’ll pause to visit Wassaw Island, said to be the best example of what Georgia’s barrier islands looked like before Europeans arrived. A national wildlife refuge accessible only by boat, Wassaw’s forests were never cleared for cotton, cattle or timber. 

Instead, we cruised down the Vernon River and up the Ogeechee through a wonderful marshland maze. As we passed inlets to and from the ocean, the sweeping tidal currents frequently flipped direction—now behind us, now against us. Toward nightfall, we anchored in Big Tom Creek alongside Ossabaw Island with good holding in 12 feet, and with porpoises playing and feeding alongside us in the golden sunset.

Charlie Jennings
Charlie Jennings welcomed us on the Indian River, near Fort Pierce, Florida. Lesley Davison

We made a short hop across St. Catherine’s Sound on Thanksgiving morning and dropped the hook in Walburg Creek, where Lesley and Jenny dinghied ashore. St. Catherine’s Island is privately owned for zoological research but accessible below mean high water to those arriving by boat.

“We stepped into prehistory,” Lesley wrote on Billy Pilgrim’s blog. “Huge driftwood trees stacked up on the sand like pickup sticks. We clambered our way around, over, under the trunks, doing our best balance-beam routines and limbo, guessing at which animals made the ­footprints coming out of the primeval ­forest of saw palmetto and ­moss-festooned oak trees.”

For our Thanksgiving feast—roasted chicken, creamed spinach and mashed potatoes served in Billy P’s saloon ­under the warm glow of LED-powered candlelight—we anchored in the placid Crescent River, just inshore from Sapelo Island. Managed by the Georgia Department of Natural Resources and the site of Hog Hammock, said to be the last known Gullah community, Sapelo is restricted to visitors with a permit from the state.

Far more accessible are St. Simons, Jekyll and Cumberland islands. Highway bridges join St. Simons and Jekyll to the mainland near Brunswick; Cumberland is served by regular daily ferries from St. Marys, Georgia, and Fernandina Beach, Florida. On St. Simons Island, Morningstar Marina offers courtesy bicycles to transient guests (dockage at $2.25 per foot); Jekyll Harbor Marina offers them in exchange for a dinghy-dockage fee ($20). We rode dozens of miles exploring these islands. Jekyll stood out, with its groomed off-road trails winding through the interior oak forests and riverside marshes to stunning unpopulated beaches and a pair of villages that make good stops for meals and libations. Cumberland Island’s wild horses, armadillos, and 16 miles of undeveloped beach lit up Lesley.

But it was St. Simons and the Strangers Cemetery that marked me with the most lasting impressions. We anchored Billy Pilgrim in 10 feet of good mud between Lanier Island and St. Simons, dinghied ashore, and Ubered to our long-anticipated rendezvous with Southern Soul barbecue. (You could order the Soul sandwich with collard greens, Soul slaw and hoppin’ John, and not be sorry.) As we hadn’t yet discovered the marina courtesy bikes, we followed directions from a guidebook to a bike-rental shop near Southern Soul. When we arrived, the shop was closed; whether for an hour or forever was hard to tell. So we started walking the couple of miles back to our dinghy. Near the entrance to a Georgia Power right-of-way, Jenny noticed a small sign: Union Cemetery, Strangers Cemetery, circa 1876. We paused in the heat, then turned down the dirt track underneath the power lines. Several hundred yards later, we hesitated when a large, feral-looking cat stood staring at us from the center of the path. We eased forward, and that gatekeeper in feline form edged aside, never taking its eyes off us. When we still saw no sign of the cemetery, Jenny entered it into her phone’s mapping app.

Despite the initial jolt from her phone’s alarm as we stepped inside, we found the place enthralling. Relatives of Jim Brown, the legendary Cleveland Browns running back and film actor, are buried there, as are influential teachers who devoted their careers to the children of St. Simons. But for us, the biggest surprise came in a quiet corner near the cemetery’s back edge: the final resting place of Bessie Jones herself. 

A book I found the next day at a St. Simons shop, Gullah Geechee Heritage in the Golden Isles, tells how she came there: “If you did not belong to a plantation, you could not be buried in a plantation cemetery. Union Cemetery was established for the people who were not born on a plantation. That is why it also has a second name of ‘Strangers Cemetery,’ since people not born on St. Simons were, in essence, ‘strangers.’ There’s a Gullah Geechee expression of ‘come yah and been yah.’ Been yah means been here, or those people who were natives and longtime residents. Come yah means come here and was the label of people considered newcomers.”

Jones, born on the mainland, spent more than 50 years on St. Simons. Still, after all she’d done to bring Sea Islands culture from here to the rest of America, Miss Bessie lived and died as a stranger in this place that’s charged with so many histories. 

We, strangers ourselves, left St. Simons hungry to return.

Any wistfulness we felt at exiting St. Marys Inlet on an early December afternoon ebb and putting Georgia behind us for now was more than tempered by our excitement about, and then our actual experience of, Billy Pilgrim’s next legs.

We sailed through two nights from Cumberland Island, entering Florida’s Fort Pierce Inlet at dawn the third day. This was a homecoming for us on several levels. Harbortown Marina (now Safe Harbor Harbortown), just inside the inlet, was the first place Lesley and I ever saw Billy Pilgrim (ex-Sam, ex-Rachel E., ­ex-Water Music), Passport 40, Hull No. 141, back in August 2017—a very happy occasion. Also, my sister’s family lives in Vero Beach, just a dozen miles from the inlet, and we looked forward to spending time with them. Billy Pilgrim entered the inlet on a ripping flood, and so intent were we to miss the shoals and avoid colliding with the outbound fishing fleet that we missed the text from Monica.

“Look left!”

My sister and her husband, Charlie Jennings, had awakened before dawn and clambered out the jetty to celebrate our arrival. They were waiting on the beach with hot coffee and apple-cider doughnuts as soon as we dropped the hook near the Indian River junction. It was a sweet reunion that carried across the inlet to the Little Jim Bait & Tackle tiki bar, where I was reacquainted with one of the best examples of what, in these parts, they call smack: tasty smoked fish dip. A Billy Pilgrim river cruise the next day with Monica, Charlie and some of their friends took us straight to the Jennings backyard dock, where Billy P spent the holiday season. As we’d experienced with our families in the fall, a developing theme—the way traveling by boat can deepen otherwise old and familiar relationships in wholly new ways—proved still more true than we’d known.

We took these warm feelings with us after the holidays, when we finally crossed the Gulf Stream. 

Pungo River
On the Pungo River in North Carolina, we pushed the autumnal daylight as we made miles down the Intracoastal Waterway. Lesley Davison

As teenagers in the early 1980s, Monica and I had spent a season sailing in the Bahamas with our parents; for Lesley, this was her first time. Across the deep Northwest Providence Channel and the shallow Great Bahama Bank between the Berry Islands and the Exuma Cays in the Bahamas, Lesley counted—and named—more than 20 shades of blue. Deep ­delicious ultramarine. Turquoise. ­Robin’s-egg blue. Tiffany blue. Powder blue. Chambray. Rich periwinkle. Cerulean. The Gulf Stream had been a “slow-motion water bed of sapphire.” Biscayne Bay was “translucent aqua, more lurid than even my childhood drawings dared to portray.”

In the Exuma Cays, for the first time, Lesley and I experienced an entirely new feeling aboard Billy Pilgrim—of taking our foot off the pedal. For nearly a year, we’d been pushing ourselves with pressing refit deadlines, pressing launch deadlines, pressing passage deadlines. Here, finally, we were able to settle in and focus on endeavors beyond simply running or fixing the boat. 

Of course, the winter weather patterns of the Bahamas—alternating cold fronts with periods of gentler easterlies, several days each—still set our agenda and sent us scurrying for shelter when the more vicious northers came through. Our only deadlines now were friends and family arriving in late March. We planned to explore some of the Far Out Islands with them.

For an idyllic month, our ambit was ­reduced from a scale that took in the entire US East Coast down to the Exuma Cays Land & Sea Park: 22 linear miles and 16 major cays. For the first time in months, we daysailed for the fun of it. We took long dinghy excursions, exploring beaches and snorkeling spots. We hiked trails, chasing iguanas and blowholes.

Times when we desired more society or proximity to a cell tower, we made our way to Staniel Cay or Black Point or Little Farmers. At Staniel, we visited the Mount Olivet Baptist Church, whose congregation arrived Sunday morning with tambourines and full-throated voices. After a good hour of solid praise, spoken and sung, and just as we thought the service might be winding down to a close, the elder organist stepped forward and raised the proceedings up another notch.

“Let God in!” he said. “Let him spear the grouper! Let him catch the crayfish!”

Alas, the god of Mount Olivet was not with us during our 2022 fishing season; we came home empty from our (for my part, admittedly halfhearted) spearfishing expeditions.

The day before our Bahamas season suddenly ended, as Lesley wrote in the blog, was a perfect day: “It started with sailing off our anchor at Big Majors Spot. We rounded the end of Harvey Cay and headed to a cove off Bitter Guana Cay, where the week before we’d taken a dinghy excursion to visit the local iguanas. We wanted to see if we could catch some lobsters. We found a couple, and used our tool, which we call the ‘French tickler,’ to rouse them out of their hidey-holes, but we weren’t quite bold enough to grab them. We saw all kinds of fish and coral, picked up a huge conch, and enjoyed the random ray elegantly flying past. An amazing underwater world of color and surprises. Back aboard Billy, we sailed off the anchor and headed to Little Bay. We showered off the salt and dinghied in to the beach to walk into town for happy hour.”

The next morning, March 4, I woke with a high fever—ending this story, and beginning another, which I’ll tell in some future issue of these pages.

Tim Murphy, a CW editor-at-large and ­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, 2022). See Lesley Davison’s account of Billy Pilgrim’s 2021-22 southbound season, at

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