Located at the mouth of the Severn River, Maryland's capital city intrigues visitors with its natural beauty and old-world charm.

Smooth Sailing in Annapolis (promo image)
The Maryland State House looms in the background as sailors head into the harbor during sailboat races, held most Wednesday nights during the summer.

A cool summer breeze caresses the city of Annapolis on this pleasant Wednesday evening, gently tossing the sailboats gathered on the Severn River.

From somewhere across the harbor, a horn sounds, and the boats begin to move. At first they seem to be a confused jumble, but soon several front-runners emerge from the pack. As they race toward the city's waterfront, some unfurl huge, multicolored spinnakers to catch a sudden gust of wind, drawing gasps of awe from onlookers spellbound by the sight.

At this time of day, visitors and residents alike have begun to relax at the city's cafes and outdoor decks, abandoning their daytime activities for more leisurely pursuits. These Wednesday night races, sponsored during the summer months by the Annapolis Yacht Club, merely add a spot of color and excitement to the already lovely canvas on which this historic town is painted.

Indeed, there are always boats on the water here, whether there's a race or not. From morning until night, you can sit on one of the benches at the city's waterfront, look out toward the Chesapeake Bay, and watch watercrafts of all descriptions--from huge pleasure yachts to tiny one-person kayaks--cruise into port. Even in the middle of the day, miniature sailboats with students from the area's renowned sailing schools frolic in the harbor.

"This is a sailing town," long-time Annapolis resident Gary Jobson confirms. "We do sailing the right way here." If anybody knows, it would be Gary. An author and ESPN sailing analyst, he won the 1977 America's Cup, the Holy Grail of sailing, aboard Ted Turner's boat, Courageous. He could live anywhere, he says, but he's chosen to make his home here in this, the Sailing Capital of the United States. Though his work takes him all over the world, he's maintained an office on Church Circle for 25 years. "Annapolis is a town where you don't have to be born here to be accepted," the New Jersey native muses. "It is a vibrant sailing community, and people really want to be here."

England native Sue Smith would agree. She and her husband, Tony, moved to Annapolis in 1980 to manufacture sailboats. Now customers from all over the world clamor for the Smiths' famous Gemini 105Mc catamaran. "Annapolis is easygoing, very laid-back," Sue says in her soothing English accent. "It's a strange place, very eclectic, but it's wonderful. I love Annapolis. I wouldn't live anywhere else in America."

Certainly not everyone in this historic town is a sailor, but there is an undeniable tie to the water. Annapolis sits at the mouth of the Severn River where it enters the Chesapeake Bay, just 35 miles east of Washington, D.C., and 30 miles southeast of Baltimore. The misty blue waters seem to beg to be explored.

While Annapolis maintains the feel of an old maritime community, there's also a level of sophistication and refinement evident here. The lovely statehouse, the site where George Washington resigned his commission as commander in chief of the Continental Army, is the oldest one continuously used for legislative purposes in the nation. Colonial buildings still line narrow streets, designed for horses instead of cars, but the merchants have changed. Instead of providing nautical services, they now attract tourists and wealthy residents. A number of restaurants and bed-and-breakfasts also occupy the historic district, catering to those drawn to this picturesque town.

Annapolis is also home to the United States Naval Academy. The 338-acre campus and its residents seem to shape life in this still-small town. Everyone here knows when the plebes arrive and when the finely educated officers graduate. Many residents adopt the midshipmen and nurture them during their four-year stay. Just seeing the mids walking across town in their dress whites fills many here with a sense of pride.

Some graduates even come to love Annapolis as much as lifelong residents such as Bill McWilliams, one of only a handful of people in town who can claim to be natives. A few years ago, he chucked his career as a lawyer, trading the stress for a life making and selling pottery with his wife, Genevieve. His goal: to enjoy his life in Annapolis.

"Genevieve has a genetic predisposition for vagabonding," Bill says, smiling at his unabashed wife. "She says, 'Let's go somewhere else.' But I don't want to. There is so much to do here, even if you don't want to do any of it. I just like having the choices."

In the McWilliams' shop, The Annapolis Pottery on State Circle, there is a platter with a Hindu proverb that seems to capture the essence of Annapolis. "Help thy brother's boat across and lo thine own has reached the shore."

This article is from the June 2003 issue of Southern Living. Because prices, dates, and other specifics are subject to change, please check all information to make sure it's still current before making your travel plans.