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Three-day bay cruise Triple the pleasure

I’m nearing the Eastern Shore.

The northwesterlies remain strong at 18 to 20 mph with some stronger gusts that could almost bury my bow in the 4- to 6-foot swells that have built across the Bay.

David Benedict couldn't have asked for three better days on his cruise to the Eastern Shore aboard Caper II, his 31-foot 1985 Hunter sloop.

The spray from the bow splitting a wave shoots up 7 feet or more, giving the foot of my jenny a good wetting. Caper II, my 31-foot 1985 Hunter sloop with a 4-foot draft, is in her element and cruising at 6-plus knots with some extended surges of more than 7 knots.

It is like summer on this early October day. I am on a single tack, a broad reach across the Chesapeake from New Point Comfort to Onancock, Va. I have my hands full. I put a deep reef in the jenny to get balance and relieve the heavy-weather helm. I actually pull the jenny in three times, as the northwesterlies strengthened by midday.

At 40 miles in a little less than six hours, it was the longest and fastest crossing of the Bay I’ve ever achieved. But that crossing was a total joy, as were the next few days of this six-day cruise from my home base at the Seaford Yacht Club in Yorktown, Va., off the York River.

Luck comes in threes

I call this cruise My Lucky Three because three is my lucky number, and I had three of the best days in succession that I could have hoped for. The days were especially clear and bright, with the kind of pleasantly dry warmth, with temperatures in the mid-70s, that you enjoy in the early fall. The winds were perfect for what I wanted to do, rotating from the northwest to the southwest, and then to the northeast. This enabled me to reach Onancock the first day, continue north to the Pocomoke River the next day, and then return south again to the Occohannock River on the third day, before crossing back to the Rappahannock (on southerlies), and finally returning to the Seaford Yacht Club (on northeasterlies again).

The winds couldn’t have been more favorable.

So I had three perfect days to go “gunkholing” on the Eastern Shore, and I found three perfect anchorages during a wonderful weather window of opportunity. It was something I had been waiting four months to do, and it all came together — with an additional bonus or two.

Caper II had the best view on the Occohannock when the sun went down in spectacular style.

It’s always a pleasure to visit Onancock, a quaint historic village with good eating places and a very prolific artist, Bill Crockett, who captures the Bay’s natural beauty with his watercolors. I’ve been there before, so I again found the south branch anchorage convenient for a quick dinghy ride into the town dock. At the end of the Onancock River, where it forms a “Y,” you bear off to starboard into the basin surrounded by homes, but stick relatively close to the port shoreline, where the pilings and docks are located. If you’re too close to shore as you enter, you can touch bottom at 4 feet in low tide. The next morning, while I was having a nice breakfast at Janet’s — a local hangout — I met a couple of guys who had sailed over from Deltaville, Va., for just one night on the Eastern Shore. There is so much more to enjoy over several days in this relatively untraveled cruising area.

Exploring new territory

I had never been in Pocomoke Sound, about a dozen miles north of Onancock, well east of Tangier Island. I was surprised by its vastness. Whether entering or departing, you cannot see the horizon to the north or south. It looks like an ocean, but generally has a very shallow bottom. You work your way north into the Pocomoke River by way of an increasingly narrow passageway. The most direct route is from the south, because the Watts Island shoal, across from Tangier Island, prevents any direct access from the west and north. As you approach the northern end of Pocomoke Sound, you cannot directly enter the Pocomoke River because of its shallow delta. Instead, you take a circuitous and narrowly dredged channel along the shoreline for a couple miles before taking the cut-through behind Williams Point into the Pocomoke River. Another couple miles up the Pocomoke River, just around an almost-180 degree turn, you’ll find the entrance to Pitts Creek to starboard. Taking the deeper channel depth to starboard, I neatly anchored just inside this creek in a small cove near where the creek turns into the river, along with another smaller sailboat with a strange Scandinavian-sounding name.

Unknown neighbor

I wondered about this boat and its inhabitant for some time. The boat’s condition did not convince me it was sailable. In fact, when I asked the owner where he was from, he told me he had sailed across from Europe some years ago and now lived up in Pocomoke City, about a dozen miles up the river. This was an absolutely isolated spot with a lot of tidewater between me and Shelltown — the nearest community on the Pocomoke — so I was very careful to lock myself in the cabin for the night. I guess all the talk about pirates in the Bahamas or off Somalia had spooked me a bit.

There was a special bonus that perfectly clear evening before retiring. It was the time of the month for a crescent moon. And there she was, just a sliver over the western sky, above some distant trees, setting toward a brilliant, deep orange-purple afterglow of the sunset. After that magnificent color in the western sky, as darkness fell with no moon or glow on the horizon from distant towns, the universe above became filled with an overwhelming sparkle of heavenly lights — stars in the millions, with the constellations sharply outlined. It was a special evening, and absolutely quiet. My neighbor didn’t make a sound, and it was a perfectly peaceful night on totally calm waters.

Heading south again

I left Pitts Creek before dawn the next morning, with running lights blazing until the sun rose. By the time I’d reached Pocomoke Sound again, the easterlies had picked up and continued to strengthen during the morning. Within four hours, I was back off the Onancock River, about a 23-mile run in good time.

I was heading for the Occohannock Creek, a bit farther south on the Eastern Shore, probably the last reasonably doable anchorage for a keel hull until you reach Cape Charles, another 15 miles toward the bottom of the Bay.

It looked like I could make my anchorage by 1 p.m. and have a relaxed afternoon. Not to be. Instead, I had a relaxed afternoon on Caper II, as the winds lightened, shifting more to the southeast, so I had to tack against an incoming tide. Finally, after dropping below 3 knots a couple miles from the channel leading to the river, I turned on the diesel and motored in, finding the channel very doable with good 6- to 7-foot depths — except where I absentmindedly ran aground by taking the wrong side of the marker. It was a senior moment for sure, since I’d gotten partway into the channel and knew how it ran. Who can figure? No harm done, and I was quickly back where I should be and shortly thereafter anchored midway up the Occohannock just before R-16. By now, however, it had become an 8-1/2-hour day.

But then there’s no rest for the weary. It was a hot afternoon, and to absolve myself of my bottom grounding, I jumped into the river, scraped off the prop, brushed down the bottom, took a deck shower from my sun-heated water bag and then treated myself to a dinghy spin up the far reaches of the river to see how the land lay. Pretty shoreline, but no gas for my outboard at the little family marina that only opens for a few hours midday. These Eastern Shore rivers are about as far away as you can get from the Bay’s Western Shore sailing Meccas.

Sensational fall sun

The big bonus on the Occohannock was the spectacular sunset. I had never before seen the sun set directly into the water of the Bay with no land or clouds of any sort to interfere. The sun was incredibly large and as bright a red-orange as I could imagine, and then it proceeded to drop quickly into the water: a third … a half … then two-thirds, and finally just a speck of bright orange light coming out of the water before going out for the night. That sight took my breath away.

The next morning, the sun rose just as clearly, but it had to come from behind the treed land mass to the east. Yet it was a continuing good omen. The southerly winds continued that day to push me neatly back across the Bay to Deltaville on the Rappahannock, where I was reunited with the marina people who I had purchased my boat from in 1998. I spent a couple really productive hours talking with and getting assistance from the diesel technician and the rigging man — something I had wanted to do for the last couple years as Caper II aged into her 20s.

In the end, my Lucky Three sail offered a perfect weather window following a low that moved off the coast and brought in a steady and reliable high that I couldn’t have scripted. Bay cruising doesn’t get much better than this.

David Benedict is a retired human resources executive living in Williamsburg, Va., who regularly cruises single-handed on the Bay

This story originally appeared in the February 2009 issue.

See related article, A tale of two tugs