All Hands on Deck

All Hands on Deck

Feeling adventurous? An overnight sail can be a fun and different way to explore Annapolis and the Chesapeake Bay

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A billow of storm clouds writhes darkly at our backs as we drive toward Annapolis on a Saturday afternoon in July. I feel a slight tinge in my chest at the thought of going out on rough water, but my husband, Pete, who has open-water sailing experience, is pumped. This is real wind.

We’re scheduled for a sunset sail on the Woodwind, a 74-foot staysail schooner that has plied the waters of the Chesapeake Bay since 1993. But right now it’s happy hour and we have some time to kill.

Arriving in Annapolis Harbor, we grab a beer at Pusser’s Caribbean Grille, a dockside restaurant offering a prime view of what the locals affectionately call Ego Alley. Yachts, kayaks, paddle boards and sailboats all vie for space in this narrow waterway, creating the maritime equivalent of rush hour on the Beltway. Savvy boaters know to bring only their dinghies into the fray. But the less experienced captains who routinely venture in to show off their big, fancy boats—and then have trouble maneuvering their way out—provide endless entertainment for the shore-bound spectators sidled up to the bar in T-shirts and flip-flops, quaffing Pusser’s signature rum Painkillers.

From this vantage point, we watch a large sailboat carrying a wedding party as it cruises around the moored boats in Spa Creek, the Bay inlet that borders one side of town. The bride and groom wave in our direction as the bar chatter turns to the 2005 movie Wedding Crashers, in which the schooner Woodwind II made a cameo appearance as the personal yacht of the character played by Christopher Walken. (A scrapbook of the filming can be found on board the boat.)

Pete and I are overnight guests aboard its less-famous twin, Woodwind, where we are greeted by a shipshape crew, neatly decked out in khaki shorts and white polo shirts. We stow our gear in our assigned “stateroom”—an amusing euphemism for quarters the size of a walk-in closet, as are typical on a boat—while Nathan, our young and energetic overnight captain, shows us how the head (bathroom) works and how to use its pump-operated, hand-held shower wand.

Returning to the deck, we choose seats near the middle on the starboard side. With its polished mahogany woodwork, the vessel feels like the sort of yacht that Jay Gatsby might have owned. The clouds above are still dark and foreboding, but the crew is raring to hoist the four sails.  

A schooner is a sailboat that has more than one mast, with the foremast as long as or shorter than the aft mast. Schooners sail fast and short-handed, so three sailors could easily manage this boat, although this day brings many more on board to cater to the 40-some passengers (mostly day-trippers) who’ve assembled on deck. Nathan recruits a few willing landlubbers to help hoist, and we’re off.

The ubiquitous scent of crabcakes wafts past us as we make the tight turn into Spa Creek. To our left, a mated pair of ospreys perch atop a channel marker. I turn to trace the charming steeples and domes of the Annapolitan skyline, whose profile is pleasantly devoid of high-rises.  

“Careful with the staysail boom,” a crew member cautions, reminding us that in high winds it can swing powerfully, and without warning.  

“And if you should plan on going for an unplanned swim, we will pick you up like a fish,” the main captain, Ken Kaye, adds with wry assurance. “It will be as humiliating as possible.”

Tanned and lean, Kaye takes a lighthearted approach to the serious stuff and seems to enjoy the corny jokes that he has probably repeated a hundred times by this point in the season.

“Best sound of all,” Kaye says, his ears tuned to the sharp snap of the sails as they fully catch the breeze. We correct our course slightly, so that the red “telltales”—pieces of cloth that hang from the foresail—are pointed straight back, confirming that we’re aligned with the wind for maximum speed.

The name Woodwind isn’t just a play on the boat’s mechanics. It’s also a nod to the captain’s history. In his former life, Kaye taught instrumental music to fourth- and fifth-graders in Connecticut (his New England accent is the real deal) and also played the French horn, the only brass instrument allowed in woodwind ensembles. In 1992, he and his wife, Ellen, both longtime sailors, retired from teaching to chase their dream. It was their daughter—now “Capt. Jen” on Woodwind II—who introduced them to the boating culture of Annapolis, which, 20 years ago, offered little for tourists craving a seaward experience.  

“The sign welcoming you to Annapolis says it’s ‘America’s Sailing Capital,’ but you couldn’t go sailing unless you had your own boat,” Kaye explains. Recognizing an opportunity, he and Ellen had a schooner built to spec and set sail with their first paying customers in July 1993. Within five years, they were commissioning a second vessel to keep up with demand. (Jen became a captain in 1996 and now challenges her dad on Wednesday nights in the Annapolis Yacht Club races. And, yes, they do take passengers out.)

“Ready for a tack! Make sure you’re seated!” Nathan yells. The sails luff (flap) as we tack and come about. I brace my feet against the side while we heel toward the churning gray-green waves. Somehow, in the middle of all this rolling and pitching, Nathan manages to serve drinks from the cash bar without spilling a drop.

Once we reach the mouth of the Bay, the captain invites us all to “take a turn at the helm.” I watch a few fellow newbies, then make my way back to the stern, plant my feet to steady myself and take over.

“Fix your eye on a distant point and stay on line with that,” Kaye advises.

Focusing on a red buoy in the distance, I grasp the wide metal wheel. As the wind and waves tug at the boat, I’m reminded why sailing is an Olympic sport. It takes real upper-body strength to stay on course.  

At the same time, there is something intrinsically pure and free about sailing. The whoosh of wind over water sweeps my mind of cobwebs, and a gust whips my hair as I breathe in deeply. It occurs to me that a sailboat is the ultimate green-energy vehicle. I am truly playing a wind instrument.

“Nine point seven knots!” Kaye yells a few minutes later. “We are sizzling!”

To our right, a huge tanker rides high on the water, and we speculate on where it is headed and what it carries. A rude speedboat cuts across our bow, violating right-of-way laws and leaving us a choppy wake to cross. My eyes scan the length of the ever-impressive Bay Bridge as—too soon for me—we head back toward the Severn River.  

Although the darkest clouds have pushed north of us, it starts to sprinkle. Within minutes, a crew member passes out ponchos by “Ralph Le Rain.” The middies at the Naval Academy aren’t out and about, but we do have a prime view of their beautiful campus, including the stadium and the distinctive green dome of the Academy Chapel, as we tack from one side to the other, zigzagging our way around the peninsula and back to dry land.

At the dock, the day passengers exit while Nathan offers dinner recommendations. He tells us and the two other couples who are spending the night on board to return by midnight.

For a town that’s so water-centric, there’s a strange dearth of waterfront dining options. We opt for a 15-minute walk across the bridge on Compromise Street—a passage so named because its creation in 1845 involved a right-of-way compromise between waterfront landowners and the City Council—and into the quiet Eastport neighborhood. There we find cozy Vin 909, a restaurant tucked into a refurbished Sears Roebuck bungalow, featuring a strong wine list and local fare such as Chesapeake littleneck clams and artisan cheeses.

After dinner, we take our time strolling back to the harbor, peeking into the McMansion-sized yachts whose crystal chandeliers hang as emblems of their owners’ healthy egos and wallets. Pete reminds me of a common saying in the boating world that goes like this: “The two happiest days in a man’s life are the day he buys his boat and the day he sells it.”  

That said, a night aboard the Woodwind truly is a luxury. We can pretend for a moment that it’s ours, without having to worry about expense or upkeep. (Replacement sails for one boat alone cost $20,000 every four to five years, and the schooners are valued at $1.2 million to $1.5 million each.)

Although it’s late, we can’t resist hanging out on the deck and chatting with Nathan as laughter from the bars carries over the shimmering black water. A few smaller sailboats are moored nearby, their masts clanking in the diminished breeze under the glow of an orangey half-moon. I watch the hypnotic play of moonlight on rippling waves as a water taxi skims to and fro across Ego Alley.

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