Going Coastal to New England


A flotilla cruise from Hampton, Virginia to Southern New England offers adventure, new friends and a taste of history  (published June/July 2017)

In the summer of 2015, my wife Carol and I thought about sailing our boat Legacy, a 2011 Hunter 39, from her homeport in Hampton, Virginia, to New England via a coastal route in 2016. Sailing in the company of some other vessels from our yacht club was also a possibility. Cruising with a small flotilla of friends would further enrich the experience. Going coastal would also allow us to meet new people and see new places.

     With this decided, we started to lay a plan. We thought about departing at the end of May 2016 from Hampton to spend the Memorial Day weekend on the eastern shore of the Chesapeake Bay, and then sail the 10 miles out the bay to make the overnight, 140-mile passage offshore to Cape May, NJ. From there, we would sail to Atlantic City, where we would leave the boat for three days so Carol and I could fly to Chicago for her high school reunion. Some of our flotilla would sail on while friends aboard a buddy boat named Starchaser would wait for us before continuing up the Jersey coast to Manasquan, and then Sandy Hook and Atlantic Highlands.

     From there, we planned to cruise through New York Harbor, the East River, Hell Gate, and then into Long Island Sound where we could take our time visiting various ports of call in New York, Connecticut, and possibly Rhode Island. At some point, a rendezvous with other boats in the flotilla was also a goal. Then, we would return via Long Island Sound, the Jersey shore, Delaware Bay, the C&D Canal to the Chesapeake Bay, and be home by mid-July.


    The “to do” list of preparations was long but Legacy is a good boat and we had her rigged for ocean sailing. On May 26, the lines were tossed, and we set course for the charming village of Cape Charles 14 miles across the Chesapeake Bay. This short, windless cruise motoring across the bay under sunny skies was anticlimactic to say the least. However, we had a great Memorial Day Weekend visiting with friends and local sailors, sampling local fare, visiting shops, and dressing as pirates for a costume contest that we didn’t win.

    On May 30, our cruising flotilla skippers listened to the weather forecast from Chris Parker on my SSB. It was not good. A nasty low was developing off South Carolina with likely movement north in a few days. Local weather had turned to a gray overcast. I evaluated Chris’ report and given the pros and cons, we all decided we would go as planned since delay would make things worse. The adventure was on.

    Our flotilla motorsailed the 10 miles down the Bay and slipped under the Chesapeake Bay Bridge into the foggy Atlantic. As I steered Legacy offshore and turned north several miles off the coast, four-foot quartering seas rocked the boat under persistent cold rain squalls. A weak seven-knot southeast wind made for a chilly time on deck as nightfall approached. We were in for 140-miles of uncomfortable motorsailing.

    Then “Murphy” struck. The batteries were not charging, voltage was dropping, the fuel gauge dropped to zero and the tachometer failed to change regardless of the throttle setting. A cursory check of the alternator showed it was turning normally and the Yanmar diesel looked and sounded fine. Given the lumpy seas, it was impossible to do any real electrical troubleshooting.

    Since we did not know our fuel burn rate because of the instrument problems and difficult sea state, I took the precaution of transferring five gallons of diesel into our fuel tank with a small electric pump.

     At that point, I radioed the flotilla about our situation. Two well-lit boats, Damn Yankee and Veritas, found us in the gloom and offered to position themselves a half mile ahead of us. With fellow sailors showing their lights, I turned off all our lights, the SSB, and the radar, using it only occasionally to conserve energy. Carol switched off the freezer and refrigerator.

    Thanks to AIS, the chartplotter, and the occasional radar fix, we knew where we were even when we lost sight of our lead vessels in the fog and darkness. It was uncomfortable, but we knew the northward slog could continue.


   Twenty-three hours after leaving Cape Charles, we found ourselves emerging from the fog into sunlight.Three hours later, we were safely tied up in a marina at Cape May, NJ. The batteries were still good. Subsequently, after several false fixes and the eventual help of a mechanic, all of our mysterious voltage and instrument problems were traced to an ignition panel plug, which joins the panel to a plug on a cable going to the alternator and a common instrument ground. The plug had loosened slightly after five years and contacts had accumulated some grimy dust. After a simple cleaning, all systems began to work as advertised.

    We enjoyed Cape May with its beautiful old houses, B&Bs, and local shops. All crews enjoyed a sumptuous lobster dinner in the evening. The following morning all boats departed except for us and Starchaser.  Frankly, we wanted to chill. We were glad we did because bad weather and the cursed fog had returned with a vengeance forcing the rest of the fleet to duck into Atlantic City.

    The following morning, our flotilla of two clawed our way through the ever-present fog into the Atlantic. Fortunately, by mid-morning all was well with the world and the fog began to lift as we sighted Atlantic City and its inlet.

    The inlet was roiled up with the wakes of countless pleasure craft, but once out of the inlet the trip to the fuel dock and marina was pretty calm. Our pick of a marina adjacent to a casino proved to be a well-run and secure choice. Leaving the boat safely tied-up, Carol and I flew to Chicago for her high school reunion. We returned three days later and left the following morning for Manasquan inlet about 50 miles north on the Jersey coast. Ducking into the inlet would break up the 80 mile or so run to Sandy Hook.

    The uneventful, but sunny trip had us mostly motorsailing with sightings of coastal cruisers like us making their way north and sometimes south. Medium size cargo craft passed in the distance while closer in we were greeted by pods of dolphins playing in the waves. Manasquan inlet came into view in late afternoon.

    This inlet can be impassable with a strong east wind. The current is swift and the tidal range was over four feet on fixed docks. As dumb luck would have it, we had no east wind and were soon moored at the fuel dock by an impressive dock crew. That evening all crews dined aboard and turned in for an early morning departure the next day.

    We were actually able to do some sailing interspersed with motorsailing the next day en route to Sandy Hook and the anchorage at Atlantic Highlands. Finally, we began to shed some of our foul weather gear thanks to warming temperatures. Rounding Sandy Hook, we snaked through various dredging vessels and kept an eye out for cargo ships, most of which were either headed to or coming from New York Harbor a few miles away.

    Contacting the Atlantic Highlands harbor master on VHF netted us a mooring ball, inside the breakwater, which we picked up on the first try with me doing the grunt work and Carol at the helm.

     For the next several days, Ron and Sue from Starchaser, and Carol and I hiked the surrounding area, checked out several restaurants, and went to a farmer’s market. Our daughter and her family who live in the area had dinner with us ashore. The hospitality and friendliness of all we met in the town, harbor, and yacht club were much appreciated.

    Our last night on the mooring ball provided more excitement than we wanted. The wind speed and wave action increased dramatically. The wind was so strong the bimini connector started to unzip before I secured it with a bungee. We clocked 54 knots during the night. Below, copious amounts of alcohol were consumed. Fortunately, day break brought quiet, sun, and a mere 12 knots of wind from the north.


    We left the mooring ball and cruised into the organized chaos of New York Harbor. I have never seen so many AIS contacts on the chartplotter. We used our VHF to alert ships of our intentions and, conversely, they told us where they were going, or where we could go. That said, the “big boys” ruled the right of way!

    Our flotilla did lazy eights off of lower Manhattan taking pictures of the Statue of Liberty, Freedom Tower and other sights as Carol assertively and continually warned me about another approaching vessel threatening disaster. We entered the East River an hour before max flow through Hell Gate. Carol had studied the cruising guide and learned that if we did this the current would carry us the entire 22 miles to Long Island Sound.

    Entering the river, we quickly hit eight knots with the engine barely turning over, and then sped up to 12 knots as we passed the United Nations, Roosevelt Island, and approached Hell Gate at the junction of the Harlem and East Rivers. At that point, I contacted a mid-sized tanker quickly gaining on my stern. The captain and I agreed I would move a bit to starboard and he would move a bit to port. Minutes later a 30-foot high steel wall you could almost touch, or so it seemed, glided past as we both followed the river to the Long Island Sound. Our total transit time was just two hours.


    Once in the sound, we sailed for another hour and entered Manhasset Bay, where we fueled up and picked up a mooring ball. The following morning, on our way to Milford, CT on the other side of the sound, we spotted two elderly ladies in a 30-foot, minimally equipped sailboat. The stern showed a home port in Louisiana. I asked if they were from out of town, or actually locals. They said,” Yes, we are from Louisiana and we are bound for Maine. This is the first time we ever took a long cruise that wasn’t on a lake”. After wishing them well, I thought you are as old as you want to be, and the spirit of adventure exists as long as you want it to live.

    We spent days in Milford enjoying this scenic New England town, which is replete with fine restaurants, a lovely town green and a convenient ice cream shop next to the town marina. We celebrated Ron and Sue’s anniversary over delicious dishes of lobster paella paired with good wine.

    From Milford we cruised to Mystic, CT, dodging lobster traps along the way. From Legacy, we launched our dinghy and used its electric engine to motor several miles up the Mystic River to the Mystic Seaport Museum. The history of 18th and 19th century New England whaling was told in countless displays. We toured the Charles W. Morgan, reportedly one of the most successful whaling vessels ever, which was built in 1841 and taken out of service in 1941. We got to see how old vessels are restored with ancient techniques.

    For example, the slave ship Amistad was in for a refit. It is the recreation of the ship that was taken over by its African slave prisoners, who were then recaptured at a New England port. The slaves were eventually freed from a U.S. jail thanks to a court defense by John Adams, later a U.S. president.  The present-day Amistad was once captained by William Pinkney, the first African-American to sail solo around the world.

    Leaving Mystic, most of the flotilla cruised to a rendezvous in Stonington, CT, famous for its New England charm, and repelling the British in the War of 1812. Beautiful old houses are everywhere, and good looking heirloom quality sailing craft lie smartly moored in the harbor. Crews of Legacy, Starchaser, Merlin, Grace, and Damn Yankee swapped stories and caught up on each other’s travels while sight seeing and enjoying meals together.


    We elected to begin the sail home as Starchaser had earlier commitments at home, and ours weren’t too much further behind. We sailed back to Mystic, explored Noank, CT, and then pressed on to Oyster Bay, NY, where we were welcomed with a picturesque sunset sailing regatta.

    Oyster Bay is the site of the Battle Ship Maine memorial, and the summer White House of Theodore Roosevelt. While President, TR laid out his foreign policy by saying, “Walk softly and carry a big stick”. His White House is now a fine restaurant and micro brewery with advertising posters of him, beer in hand, saying “Walk softly and carry a big growler you will go far!”

     From Oyster Bay, we retraced our route through New York harbor and down the Jersey coast. Underway to Cape May in sunny warm skies, we spotted numerous dolphins and a whale to say nothing of experiencing great sailing. Hull speed plus was the order of the day.

    Our early morning departure from Cape May up the Delaware Bay saw us motorsailing in light winds, marked by non-stop ship traffic and a lone guy in a 20-foot row boat rowing up the bay. At least he was going with the tide.

    In late afternoon, the wind piped up to 20 knots as we waited for a massive car carrier to exit the C&D canal. The captain asked if I could move to the starboard side of the Delaware Bay channel to which I replied Legacy will be happy to go outside the channel! The C&D canal itself is 450 feet wide and for our passage through it was devoid of any other ship traffic.

    As the sun was starting to set, our little flotilla ducked into a rustic marina off the side of the canal in Bear, DE. It actually had a traffic light to let you know when it was safe to enter or exit the marina.

    The following morning, we completed our trip through the canal and entered the Chesapeake Bay. We decided to take a detour to visit the colonial town of Georgetown, MD, so we turned east into the beautiful Sassafras River. It was then Carol and I heard a mayday from an overturned sailboat at the mouth of the river. By the time we got there, the Coast Guard had rescued two crewmen and the sailboat was being towed to safety.

     From Georgetown, we sailed in tee-shirt weather down the bay and stopped in Annapolis and Solomon’s Island before heading home to Hampton. A month had passed and we had fulfilled our quest to sail Legacy to New England. We’d made new friends and visited charming and historic ports. And, we had the pleasure of sailing with a flotilla of friends.

Curtis Morris is a retired U.S. Air Force Colonel and international security consultant. He does freelance writing, and is a presenter to sailing groups. He is the Past Commodore of the Old Point Comfort Yacht Club in Hampton, VA.

Author: Curtis Morris, Jr.


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