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A sailboat floats at the dock. From the Annapolis harbor, it's only a couple of miles to the wide open Chesapeake Bay. (iStockphoto)

Life Aquatic

The sailing world docks in Annapolis

In 2005, some of the biggest names in sailing chose Annapolis as the home of National Sailing Hall of Fame. With a temporary exhibit now at the city dock, a permanent exhibit will open in the near future. And from May 4-6, Annapolis will host the annual Maryland Maritime Heritage Festival, an event filled with music and other entertainment, all focused on the area's connection with the water.

Even though these events and museums draw crowds, the locals don't need an excuse to turn their attention to the water. For people like Jennifer Brest, it happens nearly everyday. On a recent day at the town's harbor, Brest's Woodwind II swayed to the wind's rhythm. She and her colleagues readied the schooner for a private charter in the afternoon. During the season, the Woodwind II sails up to four times a day on cruises open to the public. "People say we are the best part of their vacation every time," says Brest, who enthusiastically showed off pictures of her and her crew with the cast of the movie Wedding Crashers. Part of the film was shot on the Woodwind II.

Brest's passion for sailing is contagious, and she points out that the sailors in town are very social and close-knit. For example, Rick Franke, the head of the Annapolis Sailing School, often helps with the Woodwind II trips. On Thursdays, Brest hosts a local music night on the boat. Who's a frequent performer? Them Eastport Oyster Boys, the band started in part by Jeff Holland of the Annapolis Maritime Museum, along with Kevin Brook. One of their songs sums up the feel of Annapolis nicely: All you need, they sing, is a "good hat, a good dog, and a good boat."

Whitney Dangerfield is a regular contributor to

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