LADY -- Charters are arranged by calling 301/268-4148 anytime.

There are two ways of looking at chartering a skippered sailboat to cruise the Chesapeake Bay out of Annapolis. An experienced sailor would want to sail his own boat and go wherever he likes. An inexperienced, would-be sailor might just sit back and dream about it, thinking the cost prohibitive.

But Captain John Barry and his "Lady," a new Ericson-35 sloop, can easily adapt to wind, weather, and the whims of either kind of passenger.

A wintertime master of the schooner "Harvey Gamage" out of St. Thomas in the Virgin Islands, Barry is spending this summer working and sailing his fast, modern yatch for hire out of the Annapolis harbor.

Charging $15 a person ($7 for students) for a three-hour sail out to the middle of the Bay, Barry also throws in free sailing lessons. He leaves from the Yatch Basin Company Dock next to the Hilton Hotel at 9 a.m., 1 p.m. and 5 p.m. daily. A 13-year-old Virgin Islands boy, Adam Berado, is his crew until August.

He also offers himself and his yatch with room for six people for $120 a day and overnight. This figures out to $20 a day per person and that includes an all-day sail and a room for the night, anchored in some quiet harbor.

Barry, a handsome, sandy-haired, 35-year-old bachelor, says "It would delight me if weekend charterers could just go ahead and handle the boat themselves. That would leave me time to do other chores on board. The boat is theirs to sail wherever they want to go. I get enough sailing as it is."

The Ericson also serves a business purpose for Bay Yatcht Agency in Eastport, the local Ericson dealer that steers people interested in Eriscons to Barry. Chartering a boat and sailing it can tell you more than any brochure or salesman can.

For cruising purposes, Barry has installed a roller-furling jib to make sail-handling easier. "Lady" has a very roomy, comfortable cockpit; wheel steering, lifelines, inboard diesel power and standing head room in two teak-paneled cabins that can sleep six. (Barry would sleep on deck, although he calls the boat home, too.) There is a full galley and an enclosed head with a shower.

When they leave the dock, Adam usually rraises the mainsail and unfurls the jibs, and the engine is shut down. The conservative Barry prefers to sail and tack out on close reaches. "It's a good teaching method," he says, "and is comfortable and fast. Why scare someone and bury the rail with too much sail? Of course, if someone wants to do it that way, I'll go along with it." Barry, a patient and calm teacher, explains the operation of the boat simply.

The summer breeze generally coming from the south usually calls for closer reaches and tacking out the Severn River and out among the big anchored cargo ships waiting in the middle of the Bay for berths in Baltimore.

Barry -- who's been sailing since he was five and also has sailed summer cruises out of Boothbay Harbor, Maine, aboard his Friendship sloop, "Lady" -- has had many repeat customer. "Some of them have gone out at 9 and then stayed on for the one o'clock sail," he says. "And some regulars have come back four or five times. I like to take out families and teach sailing, and I especially like working with children.

No one has ever asked to cut a sail short. "I prefer to take it nice and easy," says Barry. "Nothing fancy. Nothing risky. Just good, sensible, comfortable sailing. Three hours is a good sail for most people." At $5 an hour, it's undeniably cheap.

To ease the routine of sailing nine hours a day, seven days a week, Barry has come up with some intriguing variations and is willing to listen to others. hHe offers sails in the moonlight, to an uninhabited island for a beach party, to big-city Baltimore, or across the small villages like Oxford, Or, he suggests watching the finishes of the Wednesday night races in the spectuclar sunset in the harbor, with someone on board who can actually explain them.

For long sails, Barry prefers that charterers provide their own food and drink, although he does offer complimentary iced tea.

The licensed captain will work "Lady" out of Annapolis until after the U.S. Sailboat Show in early October.He plans to leave for the Virgins in mid-October to take over command of the "Gamage." There he will bareboat (no paid crew) "Lady" out of St. Thomas for $950 a week.

Is it really a good life, everyone wants to know, this sailing about from one place to the next; this following the sun from one season to another with no wife, no family, no house in the 'burbs, no car to maintain, nor job to commute to? Tell us, John-boy. At the age of 35, is a life like yours really all it's cracked up to be?

Deep furrors appear in Barry's tanned forehead and he tugs at his white peaked cap and runs his fingers through his long, blonde hair. "That's a tough question," he says. "But if you really want to know the truth; the honest truth . . . We'll, yes. It is."