By Gary Lee
Washington Post Staff Writer
Sunday, July 16, 2006; P01

By Newport's lofty standards, my fantasy seemed modest.

After all, this Rhode Island seaside enclave -- where tobacco heiress Doris Duke once kept a pair of Arabian camels in her antiques-filled home -- is a destination for highbrow folly. One favorite pastime for locals is repairing to the polo field for a sip of bubbly and a peek at a match. Newporters and tourists alike favor the mansion known as Astors' Beechwood, where actors posing as the kin of mogul John Jacob Astor greet visitors as if they were guests of the family. And in the evening, the scene shifts to the Spiced Pear, dining spot of the moment, for a cut of Kobe beef, a taste of tandoori venison or a nibble of sake-poached pear.

All I wanted to do was sail.

At first, yacht watching -- spectacular in these parts -- was thrill enough. In a slow drive last month along Newport Harbor, all sorts of nautical eye candy was on display. Stately schooners with walnut and brass interiors. Grand, custom-made yachts in full-masted majesty. Elegant classic 12-Meters, including the celebrated Weatherly and Intrepid, both winners of the coveted America's Cup.

That meander took me through Newport's small, boutique-packed downtown and then south along Ocean Drive, which hugs a pristine stretch of Atlantic coastline. Finally came a chug up Castle Hill and its grab-the-camera panorama of Narragansett Bay, whose water was regal blue and its islands lush and emerald green. But it was the fleet of Shields sailboats -- compact 30-foot racing craft jockeying for position at the start of a competition -- that caught my attention.

A chap dressed in slacks and Topsiders apparently noticed my excitement. He turned out to be Bob Milligan, veteran of many a sailing race and owner of Astors' Beechwood. "Maneuvering one of those boats is much more of a pain than it seems," he said. "Better to take it all in from a pretty perch up here."

The warning came too late. I could already hear sails flapping overhead and feel the wind at my back. For once, transforming a flight of fancy into reality would be simple enough.

Or so I thought. Sail Newport, known for honing locals' nautical skills, assured me that as part of a two-hour course, I could get out on the water with an instructor. (Complete novices like me need about 12 hours of supervision before sailing solo.) In two days, I would have my appointment with a boat.

* * *

That left just enough time to hit the high points of this city, about 35 miles southeast of Providence. With just over 28,000 inhabitants -- a mix of seamen and women working at the Newport Naval Station, landed New Englanders, service workers in the city's tourist industry and students at Salve Regina University -- spread over nine square miles, it's small enough to explore with ease.

First stop: the International Tennis Hall of Fame on Bellevue Avenue, Newport's toniest street. The shingle-style building was constructed in 1880 as the Newport Casino, a clubhouse for summering aristocrats; today, an array of finely manicured grass courts still gives the place a rarefied look. Once these were hallowed grounds, the domain of the racquet set. These days, anyone with a standard-issue Wilson racquet, $35 and a set of tennis whites can bat at balls here for an hour.

The Hall of Fame is a sprawl of plaques and displays -- including historic photographs, a gamut of tennis fashions and other memorabilia -- paying homage to its 200 or so inductees. The exhibits tell memorable tales from the annals of tennis, including the 16-year rivalry between Chris Evert and Martina Navratilova. The tense finale between Australian Evonne Goolagong and American Billie Jean King at the 1974 U.S. Open (King won). 1975's brilliantly orchestrated four-set faceoff between Arthur Ashe and Jimmy Connors at Wimbledon, which made Ashe the first African American to win that exalted singles competition.

In high sports mode, I headed to Glen Farm, a set of polo fields perched amid lovely stone barns six miles north of downtown. There, in a rush of fine horses and sweaty players, the U.S. national team was facing off against Scotland.

The real show, though, was in the stands and on the grounds. The hats, led by several versions of the shell-shaped headwear favored by Queen Elizabeth II, had even more stare-right-at-me appeal than those seen in church on Easter Sunday. The men -- sporting either seeksucker and white bucks or the Total Ralph Lauren Look -- could have stepped out of a prep school handbook. Several groups, huddled over tables covered in checkered cloths, sipped Veuve Clicquot champagne and munched on canapes and chocolate-dipped strawberries.

The tailgate parties, celebrating the U.S. team's victory, lingered on well after the game was over.

At dusk, my traveling companion Eddy and I joined a sunset cruise with a dozen other visitors aboard the American Eagle, a sleek beauty with a star pedigree. It sailed in the America's Cup race in 1964, and media titan and yachtsman Ted Turner was once an owner. Current owner Herb Marshall took us south to Newport Harbor near Castle Hill. We then tacked and headed north, turning back near the Pell Bridge. Marshall pointed out the sights along the way, including Hammersmith Farm, the childhood summer home of Jackie Onassis, and Fort Adams State Park, where jazz greats go wild at the annual Newport Jazz Festival.

On the return trip, I calculated the amount of time before my turn at the tiller. Thirty-six hours to go.

* * *

A slightly cloudy Saturday offered just the opportunity for a look at Newport's premier attraction: the stone "cottages" (read: palatial estates) built as summer residences for the Vanderbilts, Wetmores and other well-off New York and Philadelphia families.

"In" New Yorkers have long since abandoned Newport for the Hamptons and other locales. And the homes, towering over Bellevue Avenue like the remains of a fallen empire, have mostly become museums. The Chanler, an elegant estate where President Theodore Roosevelt was a frequent visitor, has been transformed into an oceanfront boutique hotel offering total immersion in the mansion experience.

In the course of a day, I visited Rough Point, the Breakers, Marble House, Astors' Beechwood and the Elms, all built for people worth more than a Powerball jackpot. After more than a century, the residences still have mega-glamour appeal, and even for the most jaded, they offer insight into a chapter of American aristocratic history.

Tromping through one mahogany-covered foyer after another, it was easy to see Old Money one-upmanship at work. At Cornelius Vanderbilt II's 70-room Breakers, the two-story dining room stood out, adorned with shafts of rose alabaster. At the Elms, a rendition of a French chateau built for coal mining tycoon Edward Berwind, the centerpiece were the perfectly styled 10-acre grounds, marvelously landscaped right down to the strategically placed marble statutes. Amid the rush of Ming vases and Louis XIV furniture at Rough Point, Duke's 49-room estate, it was the master bedroom -- where nearly every piece of furniture was covered in mother-of-pearl -- that took the prize.

Those who can see only a couple of the mansions should start with Marble House, built between 1888 and 1892 for William K. Vanderbilt (grandson of Cornelius). Modeled after the Petit Trianon at Versailles, the interior -- a riot of marble in pink, yellow and every other hue -- is a work of art that trumps all the others.

If you don't have the time or resources to go inside the cottages (tours range from $15 to $25 a person), consider a stroll along Cliff Walk, a trail that runs for 3 1/2 miles along the craggy Atlantic Coast. The backs of many mansions, including finely sculpted gardens, are visible along the route -- and make even the front lawn of the White House seem a bit paltry.

* * *

Finally, the sea called. My sailing lesson -- a half-hour orientation to the boat, followed by two hours out on the bay -- started on a sunny morning at a picnic table on the harbor near Fort Adams. Brian Kelley, a dark-haired 23-year-old with the spunk of a third-generation sailor, was my instructor.

He started with "chalk talk." Drawing a diagram of a boat on a small blackboard, he explained the major parts. The sheet, the line wrapped around the winch, is used to ease the sail in and out. The tiller, attached to the sail frame, is used to steer. The boom keeps the sail extended. My head began to swirl with sailing terms.

"If you can grasp how these parts work, it will be easy," Kelley said. "If you can't, we have to keep going over it until you do." The only way to learn, he added, was to hit the water. With that, Kelley, Eddy and I climbed into Barking Mad, one of the J-22s, the 22-foot boats that Sail Newport uses for training.

"Grab the tiller," Kelley yelled. "You're on."

And so I was. As we headed into the bay, passing schooners and other vessels, Kelley explained the traffic rules. He also showed me how to watch for wind shifts and adjust the sail accordingly. Finally, he fell silent, allowing me to learn from trial and error. I encountered both. Tacking, or shifting the direction, required particular agility. In a harrowing moment, a strong gust forced me to heel until the port side of the deck was close to the water. Eddy clutched the starboard rail and grimaced.

After a couple of hours, I had calmed Barking Mad. As the wind picked up, I tacked and headed for shore, sometimes moving up to five knots. It felt glorious. I was sailing.

Gary Lee will be online to discuss this story at 2 p.m. Monday during the Travel section's weekly online chat at http://www.washingtonpost.com/travel.