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Chesapeake sailors ‘do a Delmarva’

As a Chesapeake Bay sailor for more than the past 20 years, one of my standing goals is to cruise the Eastern Shore — that beautiful maze of rivers, creeks and anchorages that define the east side of the bay. But my ultimate goal, like many other Bay sailors, has been to cruise around the Eastern Shore.

“Doing a Delmarva,” as it’s known, means to circumnavigate the entire peninsula that embraces almost all of Delaware and sizeable chunks of Maryland and Virginia, from which the three-state region gets its name. This roughly 500-mile circuit spans the entire length of the Chesapeake Bay to the west and nearly 200 miles of the Atlantic Ocean to the east. Cape Charles and the Chesapeake Bay Bridge-Tunnel mark the southern turn of this watery loop, while the 15-mile Chesapeake & Delaware Canal completes the northern link between the Chesapeake Bay and Delaware River.

Not only does this voyage offer an open-ocean, two-day passage (if you’re lucky), but it also includes Delaware Bay — known for its witch’s brew of strong tides and currents, tricky shallows, fog, storms and heavy freighter traffic.

Bay sailors looking for adventure on the water are likely to find it somewhere on a Delmarva.

Assessing the options

Sailing the Delmarva is a relatively new trend to local pleasure sailing.One of the earliest accounts on record is the 1975 book, “Western Wind, Eastern Shore,” by Robert deGast, who took four weeks to make the trip alone in a 22-foot sailboat. At the other end of the speed and comfort spectrum is the U.S. Naval Academy, which uses the Delmarva as a training exercise twice each year. Plebe crews sail the course non-stop in the academy’s blue-hulled Navy 44 offshore racer/cruisers, returning to Annapolis in as little as four days.

But few cruising sailors go to either extreme, and there are options available to those with a week to spend, some cash to spare and a thirst for a little adventure.

Those without a boat, or sailors seeking professional instruction on coastal cruising and navigation, can turn to the Maryland School ( of Sailing in Rock Hall, Md. The school runs several Delmarva expeditions each year, with a professional captain leading four or five student sailors on a week-long circuit aboard an oceangoing yacht. The $1,500-per-person tuition (food included) immerses the student in thorough, rigorous and hands-on instruction.

Reasonably experienced sailors with sound boats who prepare carefully can head out on their own — which three of us did last spring aboard Bearboat, my small but sturdy 26-foot Island Packet sloop.

Casting off from our dock near Galesville, Md., on a Saturday in early May 2004, Ken Dalecki (a former boss), Woody Leach (a dock neighbor at Chalk Point Marina) and I returned the following Saturday, 475 memorable miles later.

Clockwise or counter-clockwise?

A skipper’s first decision is which way to go around the Delmarva: counter-clockwise (up the Atlantic, down the Chesapeake) or the reverse. The two major factors to consider are prevailing winds and tides. In this region, the wind usually blows from the west toward the east. That means if we went counter-clockwise around the Delmarva, we’d be likely to have favorable winds heading north in the Atlantic — but unfavorable winds heading west in the Delaware Bay. Given the typically strong tidal currents in the Delaware, fighting a prevailing headwind would mean a slow, wet, stomach-churning ride up to the C&D Canal.

For these reasons, most sailors choose to go clockwise around the Delmarva. Taking this route, if the prevailing winds hold, allows sailors to time the leg down the Delaware from the C&D Canal to Cape May on an ebb tide with a good chance of having the wind comfortably at their back. Of course, this means the prevailing winds are likely to be unfavorable on the ocean leg of the voyage, but tides or shallows are no worry and Cape May, N.J., or Lewes, Del., make for good ports to wait for better weather, if necessary.

In our case, I bet on the prevailing winds and went clockwise— which paid off well. As we started our voyage from Galesville, a stiff but manageable 25 mile-an-hour wind blew out of the southwest, creating ideal conditions for our first leg up Chesapeake Bay. Just off the red entrance buoy to the West River, we turned off the engine, headed northeast, and raised Bearboat’s red-white-and-blue spinnaker for a sunny day of exhilarating sailing at its best. Passing Annapolis, we bobbed and weaved our way through the colorful fleets of racing sailboats that crowd the waters off the capital city on warm weekends, and soon glided under the main span of the Chesapeake Bay Bridge.

By sunset we were passing the Sassafras River. Ken and Woody contentedly wolfed down the first of several dinners I cooked up in the galley. By 10 p.m., we were motoring up the western arm of the C&D Canal; and around midnight we dropped anchor in the dark harbor at Chesapeake City — an excellent one-day run of almost 70 miles.

The Delaware

After a quick walk around Chesapeake City early the next morning, we motored east through the C&D Canal, passing several large freighters in the drizzle and mist, and entered the Delaware River with an ebb tide speeding us downriver. The topography of the Delaware is much flatter, less sheltering, and more industrial than the Chesapeake, with a lot of freighters, oil tankers and chemical barges heading to and from the industrial region that stretches from Wilmington to Philadelphia. Because of the Delaware’s notoriously abundant shoals, these huge vessels are forced to stay in the deep but narrow shipping channel; all recreational boats (including sailboats) are required to give way, either by squeezing past along the edges of the channel or keeping to the shallows.

With these concerns in mind, I managed to plow some new ground in the Delaware by avoiding the shipping channel entirely. Because Bearboat has a centerboard and very shoal draft, I kept us well north of the channel — a little too well north, as we discovered when our rapid passage downriver came to a sudden, lurching stop on a sandbar several miles below the Salem nuclear power plant.

For once, however, the Delaware’s rough weather (and the relatively soft sand) actually helped. Each crest of the three-foot waves would lift us off the bottom just long enough to inch the boat forward, and with engine and sails straining we slowly staggered back to deeper water. It took only 20 minutes or so to bounce across the sandbar and float free again (though it seemed a lot longer at the time). Our brawny little boat took the beating in stride, with damage done only to the skipper’s pride.

Not long after our escape from the sandbar, we entered the welcome shelter of the Cohansey River, on the New Jersey side of the Delaware Bay, which offers the only convenient harbor of refuge between the C&D Canal and Cape May. Winding, deep and marshy, the Cohansey has very strong tidal currents and legendary mosquitoes, which can make overnight anchoring in the river a dicey proposition. But we were too early in the season to feed the mosquitoes, and avoided the anchoring problem by motoring upstream and tying up to the floating docks at Hancock Marina in the tiny hamlet of Greenwich. That night the crew enjoyed hot showers, fresh seafood and a wonderful night’s sleep.

The next morning brought light winds, low clouds and rain, forcing us to motor the rest of the way down to Cape May. True to the Delaware Bay’s reputation, just as we felt the first big ocean swells under our keel, the tide began to turn against us, a cold, heavy fog settled in and all traces of land dissolved in the mist. Without our GPS unit, finding the small western entrance to the Cape May Canal would have been quite a challenge, especially in fog and fading daylight. With it, we arrived precisely at the narrow entrance jetty. Passing an outbound car ferry heading south to Lewes, we slipped into the canal and motored slowly against the tide to the safety of Cape May Harbor, tying up at Utches Marina. After dinner ashore, Ken, who knows the town well, led us on a dark and drizzly hike through the town’s charming historic neighborhoods.

The Atlantic

As our jumping-off point to the Atlantic, Cape May was where we reprovisioned all our food supplies, topped off fuel and water tanks, rigged up the radar reflector, double-checked the engine and all other systems on the boat, and waited for good weather. The 180-mile passage between capes May and Charles takes at least 30 hours non-stop under ideal conditions, meaning we would have at least two days and one night at sea.

Luckily, we didn’t have long to wait. The rainstorm that had brought us into Cape May passed through during the night. The next day dawned with a cold, crisp sky, near-perfect northwest winds and — most importantly — a clean forecast for days to come. After some final provisioning, showers, and breakfast ashore, we motored out of the eastern channel of the harbor, raised our sails off the big red “2CM” entrance buoy, and bore off almost due south through four- to five-foot swells — a lively ride for us, but calm for the open sea. The roller coasters of Wildwood, N.J., visible to the north up the coast, quickly faded astern, as did the lighthouse of Cape May soon after.

By dinnertime we were about 15 miles out from Ocean City, Md., with the tops of the highest hotels barely visible in the orange rays of the setting sun. Almost as soon as the sun dipped below land to the west, a huge full moon rose out of the ocean to the east, providing a spectacular twilight welcome to our long night at sea.

Unfortunately, about this time the wind weakened and shifted to the southwest — almost dead ahead — forcing us to start the engine and motorsail to keep on course and schedule. Steering by compass, we splashed and bounced along a south-southwest course through the cold, black night, watching the brilliant, blue-white moon arc slowly across our bow.

Even a relatively short passage such as this requires certain precautions. With three international shipping lanes converging at the mouth of the Delaware Bay (from Europe, Africa, and South America), we had crossed that area quickly and kept a sharp lookout for ships heading in either direction along the coast. All of us wore life jackets and harnesses with tethers clipped into well-secured lifelines (especially at night) whenever on deck. To ward off cold and fatigue, we rotated helm duty every hour-and-a-half and kept hot tea and snacks close at hand. Ken, Woody, and I shared similar professional backgrounds and had complementary sailing skills: I have sailed extensively offshore and at night, Ken is a Navy veteran who never gets seasick, and Woody is an experienced bay sailor and boat owner, capable of taking over if seasickness or injury struck. Not by accident, we had a skilled, competent, and congenial crew.

Since my boat does not have radar, I had carefully scheduled this offshore leg of the voyage to coincide with the full moon for maximum nighttime visibility — a wise decision, as it turned out. During the night, we encountered numerous oceangoing trawlers slowly dragging fishnets far astern, all but one of which was properly lit and easily visible. But about 3:30 a.m. in the Virginia waters off Assateague Inlet, we suddenly came upon a fishing trawler running dark about 200 yards dead ahead and closing fast, visible at first only by the dark hole it formed in the sparkling moonlight reflected in the ocean waves. As we quickly changed course and bore away, a hand-held flashlight blinked twice at us and a faint red running light flicked on — but even this went off again as soon as the mystery boat fell astern. The marine radio, which we monitored constantly, remained silent.

Back in the Chesapeake

Shortly after dawn, the distinctive skeletal iron tower of Cape Charles Lighthouse came into view (at 191 feet, the tallest of its kind in the nation), and the wind sputtered to mere puffs. It took us until late afternoon to motor under the North Channel span of the Chesapeake Bay Bridge-Tunnel, officially marking the end of our ocean passage and our return to Chesapeake Bay.

The closest major harbor at the mouth of the Bay is Little Creek (farther south, near Cape Henry), but we headed north to the small hamlet of Cape Charles Harbor, about 15 miles up the Delmarva coast. Once the major ferry port between the Eastern Shore and Norfolk, Cape Charles Harbor became a virtual ghost town after the Bay Bridge-Tunnel opened in 1964. That sad history is reflected in the town’s collection of boarded-up buildings and tiny harbor that offers nothing but a bulkhead to tie up to. But after 32 hours at sea, it felt wonderful to get off the boat, walk on land again, and look forward to a calm, motionless night’s sleep.

Cape Charles Harbor is also a popular overnight stop for many watermen from Smith and Tangier Islands and elsewhere around the southern-bay area, as we discovered shortly before dawn the next morning when we were awakened by the heaviest Eastern Shore accents I have ever heard. Lying in my bunk listening to the watermen’s banter and preparations for another day of hard work on the Bay, I found large parts of their conversation unintelligible. Reportedly derived from the Old English brogue of America’s earliest settlers, the Smith Island/Eastern Shore dialect is one of the oldest and most distinctive regional accents in the United States.

After breakfast later that morning, and pouring the five-gallon jug of spare diesel into Bearboat’s nearly empty tank, we continued up to Tangier Island, just below the Maryland-Virginia border in the middle of the Bay. Like neighboring Smith Island to the north, Tangier’s economy depends almost entirely on the Bay and what its residents can catch from it; unlike Smith, which is rapidly eroding, Tangier still has enough landmass and elevation (little and low as it is) to support a thriving community. The entrances to Tangier’s harbor are lined with many crabbing sheds and docks, all built on pilings driven into the shallows and forming watery “streets” that boats follow in and out of town. On land, cars are rare, and bicycles, electric golf carts and walking are how people get around. Like Venice, Italy, the character and fate of these island communities depends on the water that surrounds, supports and threatens them.

Early the next day we motored out Tangier’s western channel and headed northwest to Solomons Island. We arrived at the dock of the Calvert Marine Museum just in time to catch the day’s last tour of the charming Drum Point hexagonal lighthouse (a cousin to the ones in St. Michael’s Chesapeake Bay Maritime Museum, and at Thomas Point south of Annapolis). Our last dinner of the voyage later that evening, at an excellent waterfront seafood house behind the museum, was topped off by a spectacularly violent lightening storm — always a treat when viewed from a dry, safe place on shore. For dessert, Ken and Woody graciously picked up the skipper’s bill.

We started our next and final day early, beating against a chilly northeast wind toward Annapolis and the start of our adventure. Late in the afternoon we arrived at the mouth of the West River and turned Bearboat’s bow home toward Galesville, closing the loop we had started eight days and nearly 500 miles before.

Looking back out toward the familiar, wide waters of the mid-Bay I have come to know so well over the years, and watching the Eastern Shore slowly disappear, I felt a strong sense of both accomplishment and regret: The Chesapeake was certainly no less beautiful or seductive or inviting to me after this long and wonderful voyage — but it was now a lot less mysterious. And somehow, it suddenly seemed a whole lot smaller.

Steve Blakely is an editor in Washington, D.C.

A few thoughts on offshore safety

Life vests, harnesses and tethers, and jacklines should be considered mandatory offshore gear and should be used any time the weather kicks up. Man overboard equipment must be ready at hand on deck and MOB drills should be practiced before leaving the slip. Falling overboard at night or any other time in the ocean can be a death sentence.

Primarily for the ocean leg, I rented a four-man inflatable liferaft (stowed under the cockpit seat) and kept a “ditch bag” nearby packed with emergency gear (including a handheld marine radio, cell phone, food and water, and first-aid kit, among other things).

For any boat with a diesel engine, one of the best safety devices is clean fuel and a clean fuel tank: Rough weather and waves will stir up the water and sediment that collect at the bottom of a tank, clogging the filters and shutting down the engine when you need it most. Diesel fuel systems should be “polished” (various commercial firms will do this at the dock) before any long trip.

If you choose to ignore that advice and get into trouble, there are two major boat-towing insurance services in the region, both offering virtually unlimited coverage for about $100 a year: SeaTow ( and TowBoatUS (; for the Delmarva, the latter offers more extensive coverage along the Atlantic coast (up to 15 miles offshore).

— Steve Blakely