Gone with the Wind

Set a course for adventure on a Chesapeake Bay boat-and-breakfast tour.

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 often get stuck and have trouble maneuvering their way out. This provides 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 I, 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 the head (bathroom) and how to use its pump-operated toilet and hand-held shower.

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 crab cakes 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. “Best sound of all,” he says, his ears tuned to the sharp snap of the sails as they fully catch the breeze.

We correct our course 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). He 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 “Captain 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 of 1993. Within five years, they were commissioning a second boat 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.)


“Ready for a tack! Make sure you’re seated!” Nathan yells. The sails luff (flap) as we tack and come about. I brace myself as 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 Bay, the captain invites us all to “take a turn at the helm.” I 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.  

Though 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 reminds 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, artisan cheeses and local fare such as Chesapeake littleneck clams.

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’ wealth. Pete reminds me of a common adage 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.”  

Keeping that sentiment in mind, we return to the Woodwind, grateful for the chance to experience its romance without the burden of 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 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.

An overnight stay on a boat is a cramped affair that requires a healthy appetite for adventure and nostalgia. Every square inch is precious, and the wooden hull comes to a point at your feet. It’s definitely amenable to those who like to “sleep tight,” as the saying goes.  

The air conditioning in our cabin isn’t working, so we open the hatch above us while Nathan tinkers. Luckily the clouds are dry, and the breeze is delightful.

Lying there listening to the harbor noises, I much prefer our berth to the nearby Marriott. With all the rocking and water, sleeping on a sailboat is a little like returning to the womb. All night I feel the rhythmic swells beneath me—a lull that remains with me for days afterward.

Up and dressed early the next morning, we chat with our fellow passengers over a breakfast of crab-and-asparagus quiche and a coffee cake the crew has nicknamed “apple crack.” We happily linger, savoring the atmosphere. The salt-tinged air feels fresh and cleansing. I wonder if I can fit a late-season sail into my schedule. n

Amy Brecount White is hoping to race with Capt. Ken and Capt. Jen this summer.


If You Go


Annapolis Harbor is roughly 38 miles from Arlington. From the Capital Beltway, take U.S. 50 East toward Annapolis. After 23 miles, merge onto MD-70 South/Rowe Blvd. (Exit 24) and go two miles. Turn right onto College Avenue/MD-450. Enter the next roundabout (Church Circle) and take the fourth exit to veer off onto Duke of Gloucester Street. Turn left on St. Mary’s Street and then go right on Compromise Street.


The Schooner Woodwind (80 Compromise St.; 410-263-7837, www.schoonerwoodwind.com) is docked at the Annapolis Marriott Waterfront Hotel and sails through Oct. 26. The boat can accommodate six overnight guests on Saturday evenings. (They’ll take a fourth couple if the guests know each other.) Each stateroom has a double bed and a shared bathroom (one bathroom for two couples). The fee of $299 includes a sunset cruise and a gourmet breakfast the next morning. Overnight parking is $25 in the lot next to the Marriott, but spaces are not guaranteed.


Chick & Ruth’s Delly (165 Main St.; 410-269-6737, www.chickandruths.com). Known for its colossal burgers, shakes and sandwiches named after local politicians, the diner is a popular spot for locals and boaters. A formal recitation of the Pledge of Allegiance is led every morning.

Dry 85 (193B Main St.; 443-214-5171, www.dry85.com). The Prohibition-style speakeasy specializes in bourbon (you can order flights of top-shelf options such as Pappy Van Winkle, Willett or Maker’s), burgers, upscale pub food and a few creative entrées. Try the pork osso bucco for $19.

McGarvey’s Saloon & Oyster Bar (8 Market Space; 410-263-5700, www.mcgarveyssaloon.com). An old-school Annapolis pub serving raw bar selections, sandwiches, burgers, more than 50 American craft beers and oyster shooters.

Middleton’s Tavern & Raw Bar (2 Market Space; 410-263-3323, www.middletontavern.com). The tavern offers sidewalk seating, bar snacks and regional seafood such as Maryland crab cakes, rockfish, oysters and clams. Entrées range from $17.95 to $36.

Pusser’s Caribbean Grill (80 Compromise St.; 410-626-0004, pussersusa.com/locations/annapolis-restaurant) has a prime location, but usually gets mixed reviews for its food. Entrées include steaks and seafood and range from $12.95 to $29.95. The bar is a popular party scene for 20-somethings at night.

Storm Brothers Ice Cream (130 Dock St.; 410-263-3376, www.stormbros.com) is a local favorite for frozen treats. A single scoop is $2.55; a 16-ounce shake is $4.50. Just try to resist the raspberry truffle.

Vin 909 (909 Bay Ridge Ave.; 410-990-1846, www.vin909.com) offers a “farm to table” menu of small plates, pizzas and sandwiches ($7 to $16), and a sizable wine and beer selection. They don’t take reservations, but we got a table fairly quickly. The dining room can be noisy.


You’ll find a host of boutiques, galleries and gift shops in historic downtown Annapolis. For a list, visit www.downtownannapolis.org.


North Bay Bed and Breakfast (9 Sunset Drive, North East, Md.; 410-287-5948, www.northbayyacht.com/Charters/SailingPackages.shtml) offers an overnight on dry land and a full breakfast, followed by a half-day of sailing on the 50-foot Gulfstar ketch Journey in the upper Chesapeake Bay. Prices start at $225 per couple for a double.

The Pintita (2639 Boston St., Baltimore; 410-435-2078, www.sailthepintita.com) provides overnights on its 43-foot Endeavor sailboat, Pintita, from March to November. Guests arrive at 6 p.m. and take a two-hour sail from the Canton area of Baltimore. Couples have the option of dining before or after the sail, and alcohol is BYO. Capt. Phil greets guests the next morning with blueberry pancakes. The sail and overnight (available any day of the week) is $350 plus tax and a 15 percent gratuity. Tours can also be arranged to depart from Annapolis.

South River Boat Rentals (2802 Solomons Island Road, Edgewater, Md.; 410-956-9729, www.southriverboatrentals.com) offers bareboat (without a captain) 26-foot sailboat rentals for overnight use (10 a.m. on the first day to 6 p.m. on the second day). The cost is $650 for four people. You can bring your own food or have meals catered for an additional fee. Longer rentals are available, and you can add a captain for $200 per day.

Categories: Travel