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A Sail Around the Delmarva Peninsula

Updated on February 24, 2016

It’s cold, it’s dark, and I’m scrunched up behind a tiny dodger, waiting for my watch to finally be over. The dim coastline of Maryland shines in the background, and the wind that started out the day with such promise has all but faded away. The words that got me in this cockpit come to mind and, once again, remind me that you should never, ever, agree to anything proposed in the presence of an open bottle of rum:

Manly men wanted for crew on a sailing ship bound for a week on the mighty Atlantic. Hard work, no pay, three squares a day and a bunk. No landlubbers or dainty ladies need apply. Inquire within.

The anachronistic want ad was a gag email sent by my bold friend as a follow-up to a chilly winter weekend in Annapolis where four chums met for pool and bonhomie in a basement tiki bar. All were experienced Chesapeake sailors; on many a weekend we had sailed our respective boats to one of the countless nooks and crannies of the bay for a raft up, and individually we had sailed virtually everywhere you can go on the Chessy. None of us, however, could claim the grand prize of bay sailing: a circumnavigation of the Delmarva peninsula.

Delmarva is an acronym created from the names of the states it is comprised of: Delaware, Maryland, and Virginia. On a map it’s the big thumb that makes the Chesapeake a bay; the circumnavigation made possible by the C&DCanal at its northern reach.

But in that basement, under the warm glow of some cold MountGay, Captain Michael, his brother Randy, Scott and myself all pledged to meet again in the spring for a men-only clockwise circumnavigation of said peninsula. We bonded, we boasted, we talked of golden sunsets, leaping dolphins, and fresh tuna on the grill. We parted with the date set in stone, a rock-solid resolve to do the Delmarva.

I expected tears and arguments from my wife of seven years when I broke the news of the stag cruise. In all our time together we had never been apart for more than a couple of days; we were married on the foredeck of our Catalina 34, and almost every mile I have sailed has been with her at the wheel and me at the sheets. I prepared my impassioned speech, hopeful that she would somehow see it my way. “Oh sure, that’s fine.” She said. “Just bring back some crab meat.”

Other emails would arrive with subject lines that sizzled: R U Ready for the Open Water, Get Out Your Foulies, and Not Your Average Carnival Cruise.


The crew re-assembled in May at Randy’s Hallberg Rassy 34, True Blue, in Galesville, Maryland. The long term forecast looked good, the wind scheduled to veer around with us as we made right turns. So we wasted no time in loading her to the waterline with fuel, water, and provisions. Michael’s wife Gail took pity on us and prepared meals for the entire week that only needed heating, and thus became our ship’s chef in absentia.

At the liquor store we told the owner what we were doing and his eyes lit up. “Sailors, eh?” he mused. “Then you need to taste some of our special rums.” He escorted us back to his windowless office and proceeded to pour out samples of liquid heaven from his secret stash

At 1200, under a breathtaking blue sky with mares tails and white caps on the water, we tossed the lines and pulled up the fenders; we were on our way north for our no-turning-back cruise.

True Blue’s Volvo engine purred and, combined with the strong southwest breeze, pushed us along at seven-knots on the flooding tide. Before long Annapolis and the ChesapeakeBridge were well behind us, the less brackish waters of the northern bay lay ahead.

Once past Baltimore and the PatapscoRiver the water’s salinity decreases dramatically, and so do the ubiquitous watermen and the salt-loving blue crabs they pursue. The wind pipes up and the waves grew accordingly; we hit 9-knots under headsail alone, and smiles radiate from all aboard. We pitch, we yaw, we stagger about, trying to gain our sea legs and avoid the dreaded mal de mer. Familiar sites & navigational lights glide by and, with the exception of a tug or two, no one is heading south. Giant markers pave the way to the C&D canal and our first stop.

Sailing is not permitted in the canal, so just pass the Oldfield Point we try to douse the headsail. A yank on the furling line produces no movement and we discover that it was unfurled too quickly and has “bird nested”. A tense five-minutes pass as the brothers struggle to untangle the drum, the recalcitrant sail flailing wildly in the 30-knot gusts.

The sheets repeatedly smack the deck and I think back to what happened once when I was foolish enough to grab those lines on my boat. I sit tight till the headsail is furled.

The 14-mile C&DCanal, has been owned and operated by the Corps of Engineers since 1919. Originally constructed to reduce the water route between Philadelphia and Baltimore by 300 miles, the canal opened in 1829 and required negotiating 14 locks. Gratefully, the locks have since been removed and the canal straightened. We motor into the anchorage basin at ChesapeakeCity and set the hook at 1900, all to the tune of a reggae band at the bar on the wharf.

Irascible Delaware Bay

Overnight the wind swung around to the northwest and is blowing hard at dawn. We learn that it is Scott’s birthday, and we agree that his present from us will be the anchorage at CapeHenlopen. Anchor’s aweigh at 0800, timed to catch slack high tide, and we carefully watch fore and aft for the working vessels that ply this busy waterway. Jack lines are laid out on the foredeck for the next leg.

Within an hour the boat speed begins to accelerate and at 1045 we are shot out into the infamous Delaware Bay. Discovered by Henry Hudson in 1609 who, like Columbus, was lost and looking for a waterway to the Far East. And he, like Columbus, died trying. We’re not lost, but we’re looking for the cape, and don’t want to end up short; there is no place to anchor before there, and turning around is completely out of the question.

I must confess I felt somewhat apprehensive; I have heard many a yarn of how miserable Delaware Bay can be; to this day, portions of its upper reaches are un-surveyed. With the wind on the starboard quarter the headsail is unfurled and the boat speed accelerates to 10-knots. Wow, that feels good!

A recent posting at the NOAANationalDataBuoyCenter website states that right whales are active in Delaware Bay, and that vessels should reduce speeds below 12-knots. That’s no problem for us, and the prospect of a sighting prompts frequent sweeps of the water with binoculars.

By noon we are well past Salem Nuclear Power plant and shooting down the ListonRange. The bay gradually widens but the good water does not, and we carefully aim for the each of the prominent lighthouses. The waves are big, and the sails do little to help dampen the heavy rolling. But, finally, it is warm enough to strip off the slickers and pass out lunch.

Large tanker ships loom on the horizon, waiting to be lightened for the trip to Philly and Baltimore. We round the light at the Harbor of Refuge and decide that, despite what the cruising guide says, anchoring near the ferry and pilot docks is a bad idea. We drop a hook just inside the breakwater and munch on birthday crab cakes. The wind howls cold all night and rocks us to a fitful sleep.

Out on the Atlantic

A clear, cold morning greets us, and after coffee, granola bars and a spirited discussion of waste disposal at sea, we make for the bar at 0930--the sandbar that is. The large square waves pound the boat and slow us to a crawl as we hobby horse for a distressing 10-minutes. The hard turn to starboard puts the wind back on our quarter and for the first time we shut down the diesel.

Ah, the solitude of the open ocean. Off OceanCity the replica of Christopher Columbus’s Nina passes to starboard, doing about 7-knots using a replica of a big diesel engine. Down goes the sun and one-by-one the stars blink on. The wind is very light and we run wing-on-wing. For many hours we see not a single boat or ship.

The clear night quickly drains the day’s heat and I pile on every stitch of clothing I have minus the gloves I cursedly left behind. Despite lights out below decks, visibility is poor and frequent references to the radar are needed to avoid those things in the night.

Without a doubt, the trip’s ultimate Zen moment comes when a blood red moon and Venus rise together at 0400--you don’t see that everyday. Steering by the stars is nice, but I have to remind myself that on this heading everything in the heavens shifts from left to right and would eventually put on the shoals of Assateague Island. So the GPS and its waypoint remain the final word on navigation.

Chesapeake Bay Bridge Tunnel & Home!

We approached the bridge and its man-made islands. I smile, the last I saw this was in 1965; a little boy in the family station wagon as we took advantage of the shortcut to Virginia Beach in its first year of operation. At the time it was hailed as one of the seven engineering marvels of the world, built for an astronomical $200 million. I think I burst into tears when my mischievous brother convinced me that I had to hold my breath as we went under the bay.

In my day I’ve sailed under more traffic on bridges than I can possibly count, but at 1430 True Blue actually sails over traffic, via the mile-long tunnel under the Chesapeake Channel. As if on cue the water turns brown, a flock of pelicans glide by, and hungry flies swarm the boat in search of bare skin for dinner; we’re back in the Chessy again.

A somnolent CapeCharles greets us with ice and a cheap slip for the night. The town is a tribute to the railroad era, and the ruins of the rail launching ramp is still clearly visible. From the marina, visitors must tramp over the several rows of working train tracks to reach town where stately 19th century homes line the neatly manicured streets. Disturbingly though, For Sale signs are everywhere.

The following morning we cross paths at the fuel dock with a sailboat doing the Delmarva in the opposite direction. They have also timed their journey well, since they will be heading north on the ocean leg with winds that veered to the south overnight. We replace the 21-gallons of diesel we’ve used so far, wish them well, and our boats diverge at the last marker.

With wind on our port quarter, True Blue begins the inbound leg of the cruise. We bisect a large cluster of fishing boats and make way for Wolf Trap light. The day turns muggy with marginal visibility and we can barely make out the markers for Deltaville.

The tide bottoms out as we lined up the reds and slow the engine. But despite the caution we bump the six-foot keel, and bump again just shy of the marina. All hands spring to the starboard shrouds and hike way out until we are free and in our slip; shore leave and SHOWERS are granted for all.

It’s trips like these that remind me that you can’t believe everything you read in a cruising guide. The “ten-minute stroll” to amenities they show on their map of Deltaville turns out to be a two-mile slog on a road with no sidewalk or shoulder. Thank god one of the kids at the marina take pity on this old mariner and give me a ride to the grocery store. Once there the woman behind the counter looks at me and grins. “You off a boat?” she asks.

The wind is still smiling on us as we make our way north and soon the lee rail is buried in the salty water. And for the first time my presence is required on the high side as rail meat. We round Cedar Point, enter the PatuxentRiver, and make our way to one of the top sailing towns in the estuary: Solomons.

From the well-protected anchorage there we experience our first storm of the cruise, which drops some much needed rain on the parched region. An awesome double rainbow punctuates its conclusion and as we feast on burritos, bawdy laughter resonates from the Tiki Bar down Back creek.

Finally our luck with the wind runs out and we are becalmed for most of the hot day’s run. The landmarks move much slower now: Cove Point, Holland Point, Poplar Isle, & KentPoint go by at an agonizing pace as we seek to close the loop. The engine reaches its highest RPMs of the trip.

At 1430 we make the big turn at the big G “1” into the WestRiver and run the shoal waters back to Tenthouse Creek where sweethearts and plane reservations await us all. But before we’re even docked the talk is not of getting off the boat, but of getting on again.

We piece together rough plans for our next adventure, this time to Block Island, and of the route we’ll take, and of the winds we’ll need. The date again is set in stone for next May. And how about that? This time there was nary a bottle of rum in sight.


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