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Ghosts of the Past – Leaving NY and Chesapeake Bound

“Barnegat Again. Aground all nite – floated off at High Tide on 9/16 – lost anchor in process couldn’t re-anchor. Tied up at Marina dock – retrieved anchor – broke motor clamp getting off.”

– J. Morris, Log of the Sailing Vessel “Legacy” – 16 September, 1986

To view all photos from this period (September 2026) see the Google Photos Album HERE.

New Jersey was a challenge for the Sailing Vessel Legacy in 1986. Strong currents, shifting sands, sudden winds, and a change of everything my parents knew about sailing in New England. It was a learning experience for us, and not an easy one. Thankfully, I have the advantage of not having to make the same mistakes in person, with the knowledge that was passed on.

Planning a sailing trip like this is a careful balancing act of: some GENERAL plans, knowing what to avoid, and a whole lot of room to be flexible when things don’t go as intended. The leg of this trip from NYC into the Delaware Bay was going to be one where I knew things I needed to avoid, but the details were fuzzy.

New Jersey was one of the things I needed to avoid.

I was married to a proud Jersey Girl for a long time, and I can tell you with honesty that New Jersey gets a bad rap. The whole state isn’t Newark, and it’s hardly Newark’s fault it’s an industrial center. The western side of the state near the Delaware Water Gap is gorgeous horse country with farmers markets and antique shops. The central corridor is passionate 4th, 5th generation and beyond immigrant Italians blended with all of the more recent waves, and boasts pizza and bagels to rival Long Island and the 5 Boroughs. The eastern (Atlantic) shore is as endless an expanse of light golden sand beaches as you could dream of, surf to play in, and endless shops and seafood shacks.

What the Atlantic shore is not, is easy for small boats to come ashore to.

The same barrier islands that give endless beaches make an impassable line of rolling breakers and zero access save the occasional inlet into the interior waterways of New Jersey.

Water they may be. Ways, less so. The average depth of the greater NJ Intracoastal waterway is 5 feet. That is 0.9 feet less than I need at a minimum, and while we went into Barnegat bay aboard Legacy, we maybe should not have. The sandbars shift readily, and despite Legacy’s very meager 3.25 foot draught, we went aground more times than anyone wants in a one week period. 

The path we took in 1986 was not going to be an option in 2026; I was going to have to essentially skip the whole of New Jersey. A long trip, along the outside barrier islands, and finding places to tuck in to sleep. Over 150 miles of travel, and the tricky Atlantic weather to contend with.

Enter my friend Zach.

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This is Zach’s default expression, an absolute peach of a human.

Zach has some experience racing on J boats, and sails a hobiecat (small catamaran) in the waters of Puget Sound. (He and I bombed around in the sound on his cat a few years ago in APRIL and I’m not sure I’ve had more fun and been more cold at the same time) Anyway. Zach wanted to come hang, and specifically Zach was keen to do a PASSAGE. 

But I wasn’t planning any passages. This leg of the trip has no multi-day, never-stop, watch-and-watch-about portions planned. It DID, however, have operation “Skip NJ” to contend with. We concocted our plan.

Zach would fly out to NYC, meet me for a couple of days, and then we would do the trip from NYC to the Chesapeake in 4-5 legs:

  • Bronx to Sandy Hook NJ,
  • Sandy Hook to the Barnegat Bay inlet,
  • Barnegat Bay to the Delaware bay approach,
  • Delaware Bay approach to the end of the C&D,
  • through the C&D canal into the Chesapeake.

Then Zach would fly back out from Baltimore or grab a bus to Philly or NYC for a flight. (Zach was smart and booked fully changeable and fully refundable tickets.)

In a completely unprecedented manner… the whole thing went pretty much as planned. 

Zach flew in on Tuesday the 15th and we took the opportunity to go into the city on Wednesday and see the USS Intrepid Sea, Air and Space museum – which I’ve long wanted to see, party because they have Enterprise, the Orbiter prototype on display, and I have a personal goal of seeing all the orbiters in person. (So far I’ve only seen Discovery at the Smithsonian, and now Enterprise.)

The 3 hour round trip on the subway in and out of the city was more than Zach was enjoying, however, and Wednesday night we kicked around the idea of heading south Thursday, instead of Friday as planned. The weather looked good for it, so we said our farewells to City Island, and got up in the dark hours of 3am to hit the currents through Hells Gate going the right way. 

Traversing New York City in the dark was surreal, with bridge lights and traffic, other ships and navigation markers making a holiday display of color, and the swift current taking us at close to 9 knots at times through the East river and into the Hudson, where we watched the early morning sun gild the Statue of Liberty and then dodged the deceptively fast catamaran ferries as we made our way down to the northern end of New Jersey. 

New Jersey welcomed us with the first bottlenose dolphin of the trip, rolling and playing in the waters of the entrance to the Navasink river. We anchored, got a swim in, and did a few little boat projects before an early bedtime to get under way around 1 am the following morning. The northern shore of Jersey also brought some much more brown and cloudy water than we’ve seen so far… and from what I recall this will be with me until I reach Florida. Adieu, looking at the bottom 10+ feet down in Massachusetts!

The trip around New Jersey went well, truthfully. We made the first half around the northern reaches and into Atlantic City – another of New Jersey’s less-than-stellar locales – in a very long day with some decent sailing, and hid from some increasing winds anchored just off one of the beaches under the neon signs of the casinos. 

The following day, leaving Atlantic City, was some serious sailing. Winds in the 15-20 knot range from our stern and a following sea of 4-6 foot heights meant that we were pushed around pretty much the whole day, but we made some DISTANCE and arrived in the Delaware bay as evening fell on the 19th of September, we sailed into the shelter of Cape Henlopen and dropped anchor in the lee of the ferry dock’s breakwater. 

The dolphin again celebrated with us by bringing their babies around, and leaping out of the water while we watched in slack jawed delight. We slept like the dead, and woke again the next morning to sail – once more downwind – up into the Delaware bay and near the entrance to the C&D Canal, the artery of the Intracoastal Waterway that connects the Chesapeake to Delaware bay. 

This moment felt significant to me, as we sat in the increasingly brackish waters of Port Penn Delaware, looking at marshland and shore birds and knowing the next morning would bring us to the Chesapeake. The Chesapeake Bay is home to a wholly different world, and I will write a love letter to it in the next installment of the blog, but knowing it was at the other end of the canal was moving.

We absolutely SMOKED the C&D canal, with zero problems and a combination of the engine and our headsail taking us through and into a truly stellar day in the bay, where we unfurled the Spinnaker and sailed downwind to a nice anchorage across the bay from Baltimore, where Zach would depart.

BOATNOTE: A Spinnaker is an extremely lightweight and oversized headsail, essentially made out of kite fabric, which can catch light winds when you are headed downwind. Racers employ them in heavier winds than I ever will, and they are commonly known in sailing slang as “the kite.” 

Waking the next morning, the weather had changed and we hurried to depart before we were wholly clobbered by wind and rain, and we nearly beat it. Our final 30 minutes approach to Baltimore included wind actually whistling in the rigging, driving rain, and the wind causing us to heel all the way over to the gunwales even without sails up. We tucked into a small bay on the outskirts of Baltimore and hid there for a couple of hours until the rain let up.

Finally we were able to make our approach to Baltimore itself. The city is surreally industrial, and the view from the water is almost wholly shipping manufacturing, construction and more. Our entire approach to the marina at the Peninsula was ducking around tankers, car carriers, and container ships. (Also a rogue log the size of a Volkswagen that we thankfully did not hit in the chop)

At last, as the sky cleared some and the inner harbor gave relief from the wind, we tied up at Port Covington Marina on the afternoon of the 22nd. It had been 6 days since we’d been off the boat and we had covered more than 300 miles, including a personal distance in one day record of 87 miles from Sandy Hood to Atlantic City.

We took much needed showers, put on clean and dry clothes, and went OUT to eat, for burgers and beer… then shopping to replenish the provisions that 2 lads made a serious dent in.

It wasn’t a passage, but it was. It was also in some ways a rite of passage. This was sailing in all its glory, terror and boredom. We surfed along waves that threatened to broach us, we motored through calms, we baked and were soaked and we watched the sun rise and set from the cockpit in colors that take the breath away. We saw the dolphins and the birds, and boats so large they hold over 3,000 cars and trucks. We cooked and cleaned and laughed and spent 6 solid and busy days in the equivalent of a college dorm room worth of space… and we’re still friends!

BOATNOTE:  “Broaching” is when a wave hits the back end corner of the boat in a way that pushes the back forward faster than the front is moving. Something akin to a semi trailer jackknifing, and it’s a “Not Good” thing. Broaching can – at the least – result in loss of steering and at worst can toss a boat sideways down a wave, potentially leading to a “knockdown” (laying the boat fully on its side) or even capsizing. 

In the morning, it was time to give my friend a hug and say goodbye. A bittersweet moment for certain, as we had done incredible things – and I was also looking forward to having my home back to myself. It’s not every friend who would even want to do this sort of thing, let alone do it with such aplomb and roll with the wild schedule and the restrictions of boat life. Love you, Zach, and thanks.

Now, it’s time to get a feel for the Chesapeake and explore where the wind (very literally) takes me. Just as soon as I weather this giant nor’easter that is on the way.

… next time!


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