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Bay Tripper

You take the high road, I’ll take the low

You take the high road, I’ll take the low

My first overnight cruise of 2008 was not my first sail of the season, as it has often been in the past. This year, I have been sailing since mid-April. The boat was ready for cruising but I was not, because of a cold and wet spring. I did replace my main halyard with a double-braided line from West Marine, since the old one was showing signs of wear. Another necessary item was a paper chart, the 2008-’09 Maryland Cruising Guide edited by Mickey Courtney and published by Williams & Heintz Map Corp. of Capitol Heights, Md.

I prefer sailing solo, but on this Memorial Day weekend cruise an anonymous, unmarried couple tagged along to shake down his new sloop for what I had thought would be our three-day cruise together. I always cruise in my own boat, but I would never have joined them anyway because they are new, middle-aged lovebirds, and three certainly would have been a crowd under those circumstances, even in a sailboat with two private cabins.

In a light northeasterly breeze and in a strong ebb, this boat owner and his ladyfriend soon caught up with me in his 35-footer in the middle of Chesapeake Bay en route to Maryland’s Eastern Shore and the Claiborne harbor. His boat draws nearly 5 feet, and my full-keel with its centerboard raised draws only 3 feet, so I cut well inside Bloody Point Light while he had to clear an outer mark. I lost them at that point, especially when an easterly header sent everyone tacking toward Rich Neck at the MilesRiver end of TilghmanIsland.

I also could cut way inside the outer mark at Rich Neck, so I sailed about as they tacked and tacked, waiting to lead the approach into Claiborne, just around the corner. A red and two greens mark the easy entrance into the creek, but I motored on to the restricted (loading and unloading only) county landing dock at the head of the creek to check out the depth, which is only 3 feet at a pier used mainly by crabbers. We anchored for the night in 9 feet of water.

Dinner and cocktails that evening at a real table in a new yacht with a refrigerator, hot and cold running water, and an enclosed head with a shower was a break for me. I sank into a luxurious settee with a backrest, plenty of headroom, and with Jimmy Buffett on the sound system for cheeseburgers in paradise.

I had mentioned earlier in planning our 19-mile cruise from Annapolis to Claiborne that, wind permitting, I would head to Oxford the next day — a 22-mile trip around TilghmanIsland, through the PoplarIslandNarrows and the KnappsNarrows shortcut near the southern end of Tilghman, and into the ChoptankRiver. The owner, in shakedown mode, seemed a bit apprehensive about dealing with those narrows on a holiday weekend and, I figured, because of his somewhat deep draft, although he had been through the narrows many times before on his previous, smaller boat. He announced a decision to motor to the WyeRiver on the ’morrow, just a couple miles away. OK, no hard feelings. But I wanted to cruise, not anchor.

At 7 a.m. I raised anchor with the help of my 5-hp Honda 4-stroke to pry loose my Danforth. A beautiful early-morning breeze out of the northeast with whitecaps waited as I rounded Rich Neck and broad-reached out EasternBay with the TilghmanIsland shoreline to port. The reach eventually turned into a downwind sail, and I rigged my whisker pole for a wing-and-wing run to KnappsNarrows, dodging a fish trap on the way that blocked the middle of the PoplarIslandNarrows and required jibing the main.

KnappsNarrows was dredged to 6-1/2 and 7 feet last year, and many large sailboats transit it without mishap, though one must be forewarned to stow all sails before opening the bascule bridge. The current can be strong, and it could be tricky rounding up in tight quarters here to drop a main with two-way boat traffic running.

At the Choptank exit, the breeze dropped to nothing, and I began motoring before the wind picked up again from west-southwest. Cutting inside the Benoni Point mark at the TredAvonRiver and the always-charming village of Oxford, I was somewhat surprised to discover the point is now a treeless island to itself. I headed into Town Creek for Cutts & Case Shipyard, a source of many stories over the decades. There’s nothing like poking around this yard and its collection of wooden yachts.

Tied up at the bulkhead under an ancient monster tractor crane used to haul and launch smaller boats, I hauled out my dinghy to scrub the hull and bottom. Later I took a nap, showered and peddled around town on a rusted one-speed yard bike as marathoners in skin-tight Lycra regalia whizzed by me laughing.

The marine forecast that Memorial Day dawn called for a strong southerly building to 25 knots by late afternoon, so I got an early start, motorsailing out the Tred Avon at 7 a.m. and into a whitecapped southerly. I rolled out the jib while rounding Benoni on a broad reach to KnappsNarrows, which I reached at 9 a.m.

Once through the bridge, having observed the dropped-sail rule of the bridge tender (not a Coast Guard regulation, by the way), I began hoisting the main while still motoring in the windless calm of the Narrows. I knew I would face a southerly blast when exiting into the Bay, serving up a long fetch of 3-foot rollers, and I decided to get most of the hoisting done while inside a lee.

At the last outside mark in the 7-foot deep channel, I again rolled out the jib and headed due north on a zero-degree course to Annapolis. Avoiding another fish trap, I broad-reached along the anti-erosion bulkhead boulders of PoplarIsland, which is being filled by dredge material as a nature refuge, replacing land eroded by the tides.

The boat wanted to go wing-and-wing up the Bay as she surfed along. In less robust conditions, I would have rigged my whisker pole, which takes some nimble dancing on a pitching foredeck for an older solo sailor like me. But it was too rough for that risky maneuver, so I rolled up the jib, which was difficult to keep filled anyway on a dead run. I was surfing anyway under a full main, with my dancing dinghy sometimes catching a wave and surfing into my transom. At the first boom, I thought a boat had hit me. Oh, hello there.

Midmorning, I called the ladyfriend to find out where they were and where they had sailed Sunday. She said they did not leave Claiborne until noon and had zero wind. Oddly, I was in the Choptank at that time and dealing with the same wind conditions. But when newly in love, the wind is of no matter, and some tend to linger at anchorages, I suppose.

She said they headed back to the WesternShore and home that Sunday, anchoring in WhitehallBay, just a short distance from the boat’s marina. The skipper, she added, had been concerned about the weather after listening to a rescue operation in the predawn hours of Sunday morning, south of ThomasPoint.

I reported my position — under way off the north end of PoplarIsland. “We had a rough night anchored in WhitehallBay,” she said, where they were totally exposed to the full brunt of a strong southerly rolling in on a 120-mile fetch that guaranteed a rocking and rolling anchorage. Next time under those conditions, I suggested they try nearby Ridout Creek, just around the corner from Whitehall, which provides a protected anchorage in 8 feet of water.

They took advantage of the big breeze that Monday and continued their shakedown out of Whitehall, this time under a reefed main. I sailed straight to Annapolis on a broad reach and was the last boat through the 1 o’clock Spa Creek bridge opening. Six hours and 27 miles in a 22-foot boat was pretty good time, as far as I was concerned, and I burned only 1-1/2 gallons of gas during the three-day weekend.

Jack Sherwood is writer at large for Soundings.