Sailing the Eastern Seaboard: The Outside Route
Our first foray into salt life—sailing nearly 2,000 nautical miles from Lake Ontario to Maine—taught my wife, Sandy, and me just how much more there was to experience than lake sailing. We’d spent years cruising the Great Lakes, but our taste of long-distance coastal cruising led us to forgo our plans to return to Lake Ontario and instead adopt coastal Maine as our new sailing home. We sold our 2018 Beneteau Oceanis 41.1 True North and bought Fregata, a 2021 Amel 50. We shipped her from Sausalito, California, to Port Everglades, Florida, where we would begin our journey north to Maine—sailing on the outside.
The Amel brought an entirely new level of complexity to sailing. It had a cutter rig, center cockpit, running backstays, hydraulic autopilots, electric furlers, a shaft brake, water maker, diesel heater and genset. Many of these systems turned out to be in less-than-optimal condition, and this was our first experience with a pre-owned vessel.
It was also our first time sailing up the Eastern Seaboard. We thought we understood what we’d encounter, but the more we cruised, the more we realized there is to see and do in this part of the United States.
We paused in St. Augustine, Florida, for repairs and maintenance, gradually tackling Fregata’s technical issues. This period of troubleshooting turned out to be a blessing in disguise: It gave us time to familiarize ourselves with the boat’s systems, build confidence in our ability to solve problems, and prepare for the challenges of offshore cruising. Excitement began to replace trepidation as we prepared for our journey through 14 states and all the natural beauty, history, wildlife and people we hoped to encounter.
Our passage north from Florida began in early May. The first navigational challenge was adapting to the shallow waters of the Southeast, a stark contrast to the deep waters of the Great Lakes and New England. With Fregata’s 7-foot draft, we had to plan more carefully and pay close attention to tides. Anchorages and harbors in the Southeast are often miles inland, making it essential to time departures with ebb tides and arrivals with flood tides to avoid battling strong currents.
St. Augustine, Florida, for instance, has such powerful tidal currents that entering or exiting the city marina safely is only feasible during slack tide. Many inlets can be dangerously rough when the wind opposes the current, adding another layer of complexity. We preferred to enter unfamiliar inlets and anchorages during daylight hours, so we took four months to explore the East Coast at a more relaxed pace, minimizing overnight passages.
Our first extended stop was Fernandina Beach, Florida, a charming town on Amelia Island near the Georgia border. We immersed ourselves in its colorful history of being controlled by France, Spain (twice), Britain and several other powers before becoming part of the United States in 1821. A bumpy 6-mile dinghy ride across the St. Marys River took us to Georgia, where we explored Cumberland Island, one of many natural barrier islands that shield the mainland from the ocean. We encountered kudzu—a parasitic vine that blankets trees and gives the landscape a jungle-like feel—and feral horses, descendants of once-domesticated animals freed into the wild.
Continuing north to Brunswick, Georgia, we began to appreciate Southern culture. The speech and mannerisms of the South are strikingly different from those of our native Northeast—and utterly charming. We were delighted to be addressed as Mr. Dan and Ms. Sandy, or, even better, “Honey” or “Sugar.” Despite our unfamiliarity, we were warmly welcomed everywhere we went.
From Brunswick, we rented a car and made a day trip to Savannah, a city steeped in history and brimming with character. Savannah’s beautiful parks include one designed by Frederick Law Olmsted, the famed landscape architect behind Central Park in New York City. Savannah is also home to stunning Victorian neighborhoods and a cobblestone riverwalk. The Prohibition Museum offered surprising insights into that chapter of American history.
As the summer progressed, so did the heat, which meant it was time to put our genset and air conditioning to the test. Both worked, but with a few issues. The generator left a puddle of oil on the engine-room floor after each use and seemed to have a penchant for eating dipstick tips. With several dipstick tips floating somewhere in the oil pan, we couldn’t tell how much oil remained, and the ongoing leak wasn’t helping matters. Sadly, we decommissioned the generator for the season, planning to have it pulled, diagnosed and repaired during the fall haulout.
On the other hand, we had great luck with spotting dolphins. The most exciting moment came when a pod of 40 or 50 dolphins accompanied us out of our anchorage in the Wassaw National Wildlife Refuge near Savannah.
We spent time in several isolated anchorages nestled amid the barrier islands, including one near Morgan Island, South Carolina, home to a population of several thousand lab monkeys, some of whom escaped and made headlines just before our arrival. Our next stop, Charleston, South Carolina, was a highlight of the trip. We docked at the new 1,530-foot Megadock, where Fregata’s 54-foot length made her look like a dinghy compared to the neighboring yachts. We enjoyed learning about the Gullah Geechee culture, created by descendants of enslaved Africans from the barrier islands who developed their own language and customs.
Our introduction to North Carolina came at Bald Head Island, a stunning, sandy island at the mouth of the Cape Fear River, with pristine beaches and welcoming locals. With a world-famous marlin fishing competition underway in Beaufort in late June, our planned staging port for rounding the Outer Banks was completely booked. This turned out to be a blessing, as it led us to Wrightsville Beach, a fun beach town that felt straight out of a 1950s beach-party movie, with some of the best surfing on the East Coast. We bravely enrolled in surf lessons, enjoying the fun (and frequent falls) into the pleasantly warm ocean water.
At Cape Lookout Bight, the southernmost point of the Outer Banks, a friendly cruising club from New Bern, North Carolina, invited us to a happy hour. We suspect they mistook us for one of their fleet, but they welcomed us nonetheless. This anchorage, surrounded by unspoiled beaches and the iconic Cape Lookout Lighthouse, reminded us of Cape Cod, a later stop.
One of our more challenging passages was the 220-mile stretch known as the “Graveyard of the Atlantic,” rounding the Outer Banks from Beaufort, North Carolina, to Norfolk, Virginia. We chose our weather window carefully. After departing in the afternoon, initially heading southeast to clear a line of shoals, we turned north for the overnight passage with a full moon, following winds and calm seas. With the gennaker flying the entire way, we made good time and arrived in Norfolk the following afternoon. Sailing far enough offshore, we caught a push from the Gulf Stream, which gave us the bluest water we’d ever seen, along with occasional dolphin sightings and schools of flying fish.
Many friends opted to meet us in the Chesapeake Bay, where we spent several weeks. Unfortunately, our timing coincided with a heat dome in July. We still couldn’t run the air conditioning without the genset at anchor, and we discovered that the Chesapeake’s jellyfish population makes swimming less appealing. Nevertheless, we enjoyed exploring Solomon Island, Oxford, St. Michaels and, of course, Annapolis.
To beat the heat, we reserved docks on the hottest nights to run the air conditioning on shore power. However, Fregata is wired for 230 volts and 50 Hz, typical of European boats, while North American shore power is 110 volts and 60 Hz. We used a step-up transformer to convert the power, but the heat proved too much for it after just a few minutes of operation. Since the transformer’s plastic housing trapped heat, I drilled holes in the housing and mounted a ventilating fan to keep it cool. This did the trick, and next season, I plan to wire the fan to turn on automatically whenever the transformer is in use.
After transiting the Chesapeake and Delaware Canal and spending a night anchored on the Delaware River, we turned south again to round Cape May at the southern tip of New Jersey. There, we managed to hook an undersea cable with our anchor. This happened in a narrow, busy harbor with strong currents and heavy boat traffic. I quickly deployed the dinghy, maneuvered to the bow, and tied a line between the cable and a deck cleat, allowing us to lower the anchor and free ourselves from the obstruction. Between the heat, jellyfish, undersea cables and smokestacks lining the shores of the Delaware River, we were more than ready to push on toward New York.
Words can hardly describe the emotion of sailing under the Verrazzano-Narrows Bridge, past Ellis Island and the Statue of Liberty, and into New York Harbor. Sailing in the footsteps of our European ancestors who sought a better life in America was a profound experience, as was taking in the Manhattan skyline from the water—a view like no other. We spent a few days in New York, enjoying the city and reacclimating to being up North. The gruffer style of New Yorkers is stark, but superficial—we found kindness here, too.
The next leg of our journey took us up the East River into Long Island Sound, including crossing the notorious confluence of the Harlem and East rivers known as Hell Gate. Thanks to strict adherence to timing recommendations, our transit was uneventful, and we thoroughly enjoyed motoring up the East River, flanked by New York City’s skyscrapers on either side.
We zigzagged along Long Island Sound, stopping in Port Washington, Port Jefferson and Oyster Bay, New York, as well as Mystic, Connecticut, before heading up Narragansett Bay to Newport, Rhode Island. Newport shares Annapolis’ sailing-crazy culture, and the harbor traffic is second to none, requiring constant vigilance. Boats were anchored off Fort Adams, where an outdoor concert was underway. Tenders shuttled people to and from moored boats, several ferry lines crisscrossed the harbor, and an endless parade of private vessels came and went.
We made a stop at Block Island, Rhode Island, where navigating the channel into Great Salt Pond felt like rush-hour traffic into Manhattan, and the anchorage resembled a Black Friday parking lot. Despite the chaos, it was worth it. The island is beautiful and easy to explore by rented motor scooter or e-bike. Mohegan Bluffs to the south and Sandy Point to the north—home to curious seals—were particular highlights.
Martha’s Vineyard and Nantucket were detours we couldn’t resist. Both islands offered quaint towns and picturesque coastal scenery. However, we made the mistake of docking at the Nantucket Boat Basin. While ideal for megayachts, the tall fixed docks and 3.5-foot tides left our deck below dock level. We were also sandwiched between large power yachts, with 25 knots of wind pinning us to the dock. Our pre-dawn departure was a white-knuckle affair, but we managed to leave without damage—or lawsuits. Next time, we’ll opt for a mooring ball.
We originally planned to round Cape Cod on the outside, but sloppy weather from the season’s first southern hurricanes made conditions unpredictable. With few stopping points along the way, we opted to transit the Cape Cod Canal and cross the bay to Provincetown. Passing by Woods Hole, Massachusetts, we heard repeated mayday calls from a panic-stricken captain who failed to provide vessel identification or location details, despite our attempts to respond. With nothing visible on AIS or within visual range, we were unable to assist. Eventually, a commercial fishing vessel reported locating and aiding the distressed boat.
Upon exiting the Cape Cod Canal, we felt a gentle thump. The water was charted at more than 40 feet deep, so we couldn’t have touched bottom. Perhaps we brushed a whale with our keel. We watched for any sign of the animal, but saw none. That unsettling experience remains a mystery.
Provincetown is an eccentric gem. It was home to poets, artists and writers in the 1940s and ’50s, the hippie movement of the ’60s, and the LGBTQ community throughout—all coexisting harmoniously with the Portuguese fishing families that settled here in the late 19th century. Nearby, the Province Lands Bike Trail offers a stunning route through unspoiled forests, dunes, ponds and marshes, providing access to the Cape Cod National Seashore. At low tide, Cape Cod Bay reveals sandbars that stretch for miles, perfect for exploration—just keep an eye on the incoming tide to avoid a soggy return. Much to our surprise, we even encountered coyotes on the beach.
Provincetown is also home to the West End Racing club, a youth-only sailing club founded in 1950 and sustained entirely by donations. This brought back fond memories of my own childhood. I learned to sail solo there as a 7-year-old, an experience that involved being unceremoniously shoved out into Cape Cod Bay in a Sunfish, left to figure things out on my own. Nearly 60 years later, I was thrilled to see the club thriving, and the volunteers were equally delighted to welcome an alumnus from the 1960s.
The passage from Provincetown to Gloucester, Massachusetts, was uneventful, though we were disappointed not to spot whales. Next, we pushed on to Portsmouth, New Hampshire. Its historic charm, vibrant culture and excellent restaurants did not disappoint. The public dinghy dock in Prescott Park made it easy to enjoy outdoor concerts—our timing rewarded us with a fantastic bluegrass performance and a magical evening of Broadway favorites.
Crossing into Maine brought a mix of emotions. On one hand, our voyage was nearing its end. On the other, we were eager to continue exploring our adopted sailing home, picking up where we’d left off the previous year. Reconnecting with familiar places like Portland, Boothbay Harbor and Camden felt like a warm embrace, while the secluded anchorages of Penobscot Bay offered endless discoveries. Maine welcomed us back with classic charm—and a challenge. Near Stonington, we snagged a lobster trap line around our propeller. Thanks to Amel’s clever design, I could inspect the prop from inside the cabin. While reversing the propeller dislodged most of the line, the final wraps required a refreshing plunge into Penobscot Bay’s 55-degree waters. Thankfully, I freed the line without cutting it, saving the traps.
After 2,200 nautical miles, four months aboard, 14 states and countless encounters, it’s hard to imagine a richer or more rewarding experience. Sailing up the East Coast on the outside is not only manageable for a shorthanded crew, but also delivers a level of adventure and natural beauty that the Intracoastal Waterway cannot match.
Dan Kerpelman is a lifelong sailor with 60 years’ experience, a USCG 100-ton Master, and US Sailing instructor who teaches, cruises, and has owned a wide range of cruising yachts.
The post Sailing the Eastern Seaboard: The Outside Route appeared first on Cruising World.