Written by Janina Birtolo for Traditions

“I am not a hotel builder…But the Ponce de Leon is an altogether different affair. I want something to last all time to come…”


Those are the words spoken by Henry M. Flagler to explain his construction of the grand Ponce de Leon Hotel in St. Augustine in 1888. They could just as well have described The Breakers or any of the other elegant hotels that Flagler built along Florida’s east coast in succeeding years. Remarkably, they also could easily describe the philosophy and belief of the Kenan family, which currently owns and operates The Breakers—a family related to Flagler by marriage and committed to his ideals of enduring service and quality.

Flagler with wife Alice

When Flagler first arrived in St. Augustine in 1878 hoping that the warm weather would help his ailing first wife, Mary Harness, Florida was still a wilderness. Although he found the weather delightful, he was dismayed by the poor hotel accommodations and inadequate traveling facilities.

Journeying to Jacksonville and then St. Augustine was an arduous process in those days, made up of a combination of overland coaches, slow-moving railroads, and stormy boat rides. One anonymous passenger of that time remarked, “There are two ways of getting to Jacksonville from Savannah, and whichever you choose, you will be sorry you had not taken the other.” Traveling from Jacksonville to St. Augustine was just as bad.

It’s not that Flagler was unaccustomed to hardship. He had, in fact, built his millions from practically nothing and fully realized that hard work carried great rewards. Born in upstate New York, Flagler began his career at the tender age of 14 when he left his impoverished family to seek his fortune in Republic, Ohio, where relatives owned a store. Having succeeded in that setting, he eventually established himself as a grain and produce commission merchant in Cleveland.

Here, Flagler formed the partnership that would lead to his incredible financial success. Joining with John D. Rockefeller, he co-founded the firm of Rockefeller, Andrews and Flagler—a company that by 1870 became the Standard Oil Company, where Flagler served as both vice president and Rockefeller’s closest associate. By 1880, at the age of only 50, Flagler was a multi-millionaire.

So it was with some sense of perspective that he first looked at St. Augustine and determined that the city deserved something better. Flagler’s first wife died in 1881, and he returned to St. Augustine in December 1883, on honeymoon with his second wife, Ida Alice Shrouds. The return visit convinced him that the area was ripe for awakening.

“It occurred to me very strongly that someone with sufficient means ought to provide accommodations for that class of people who are not sick,” Flagler told a friend, “but who come here to enjoy the climate, have plenty of money, but could find no satisfactory way of spending it.”

Thus it was that, in 1885, Flagler began building the luxurious 245-room Ponce de Leon Hotel. To design this “best in America” hotel, he chose two relatively unknown architects from New York, John Carrere and Thomas Hastings, and turned them loose. Living up to Flagler’s expectations, the designers spare no expense and created an elegant Spanish Renaissance-style palace—replete with loggias, porticoes, red roof tiles, and mosaic and marble work create by Italian craftsmen.

Tiffany provided some 75 stained glass windows for the vaulted dining room, and George W. Maynard, whose work adorns the Library of Congress, fashioned numerous allegorical murals. “This was not just a hotel that had been casually decorated by a group of commercial artists; it was conceived and executed by the best craftsmen,” noted Richard Pelter, head of a crew of eight conservators who recently completed an extensive restoration of the hotel. “Technically, it was quite brilliant the way they put the whole decorating scheme together. There’s great freedom and passion in the designs, in the murals and symbolic figures, every face is unique, each position slightly different.”

Needless to say, no one in St. Augustine had ever seen anything like it. Nor had many of the rich socialites from the New York area, who began flocking to warm winters in these incomparable surroundings. To accommodate them further, Flagler began, also in 1885, to establish a standard gauge railway. Eventually, his railroad would stretch along the Sunshine State’s entire east coast, even down to the southernmost point of Key West.

But nearly 20 years before he made it to Key West, Flagler had another very important stop to make—Palm Beach, where he would build his most famous and most exclusive hotels.

When Flagler arrived in Palm Beach in 1893, it was a sleepy, palm-laden (the result of an ancient Spanish shipwreck) barrier island not unknown to Northern vacationers but without any remarkable facilities. The Coconut Grove Hotel was about the only lodging place, and it was little more than an eight-room addition to “Cap” Dimick’s home.

Flagler’s visit was accompanied by rumors that he planned to bring his railroad and build one of the largest hotels in the country. When he purchased the McCormick homestead for an unheard of $75,000, the truth of the rumors was realized, and the area’s first real estate boom began, pushing prices to anywhere from $150 to $1,000 an acre.

Flagler began his new “paradise” with the building of the Royal Poinciana Hotel on the shore of Lake Worth. More than 1,000 men, some of them the finest artisans in the world, worked to complete in less than a year what would become the largest wooden structure in the world. The complete hotel was so vast that bellboys rode bicycles in the halls, and as at the Ponce de Leon, no expense was spared to make this the grandest of winter resorts.


Breakers Hotel
Breakers Hotel

In 1895, the following year, Flagler undertook the building of an annex to the Royal Poinciana. The Palm Beach Inn (later to become The Breakers) was intended as an oceanfront outlet for guests who might like to swim or stroll the beach. The “Inn,” however, proved as popular as the resort, and Flagler subsequently enlarged the facility. By 1901, he renamed the inn The Breakers, in line with his guests’ penchant for listening to the nearby surf.

Palm Beach soon became the most popular of winter resorts for society’s elite. Drawn not only by the pleasant climate but also largely by the luxury and elegance of Flagler’s hotels, guests enjoyed the finest of outdoor activities, gourmet dining, fancy dress balls, and incomparable surroundings. The original Breakers burned in 1903, but Flagler ordered it rebuilt immediately, and guests continued to enjoy the best life had to offer.

That legacy continues to this day, although the Royal Poinciana has long since been demolished and the current Breakers is one Flagler never knew. The Kenan family was just as unfamiliar with the luxury hotel business as Flagler had been with the Ponce de Leon when one of its members married Flagler in 1901. But, like Flagler, the Kenans proved to be quick learners, astute business people, and committed to offering their guests only the finest.

The relationship began following the institutionalization of Flagler’s second wife. Drifting into madness, Ida Alice grew convinced that the czar of Russian desired her, and she turned homicidal toward Flagler. By the time Flagler was granted a divorce, he had made the acquaintance of Mary Lily Kenan, a lovely woman 37 years younger but who shared his zest for life and his appreciation for living well.

Mary Lily hailed from an established North Carolina family, born and bred to the plantations and esteemed members of a genteel society. Philanthropists and supporters of education for more than two centuries, the Kenans—Mary lily’s great, great grandfather to be exact—had helped to found the University of North Carolina at Chapel Hill. Her ancestors and descendants proved to be astute and successful business people, but it was through Flagler that Mary Lily realized the fortune that would deem her the second wealthiest woman in the world.

It was for Mary Lily that Flagler built the incredible Whitehall, a Palm Beach palace that cost $2.5 million (in 1901 dollars) for construction and another $1.5 million for furniture, tapestries, artwork, and accessories. Resurrected by his granddaughter, Whitehall is now the Flagler Museum, and visitors can experience firsthand the same attention to the finest quality and detail that Flagler lavished on his hotels.

With Mary delightedly ensconced in Whitehall, Flagler pushed on with his railroad, helping to establish Miami and eventually, after years of fighting the wilds, water, and hurricanes, reaching Key West. The latter was accomplished in 1912. Flagler died the following year.

At the time of his death, Flagler was still estranged from his only son, Harry. Although he willed blocks of Standard Oil stock to Harry and Harry’s three daughters, it was to Mary Lily that Flagler left the bulk of his estate—an estate that included at least $100 million in stocks, bonds, and Florida properties.

And so it was that the Kenans became hoteliers. With Mary Lily’s death, control passed to her brother, William R. Kenan, Jr. (who had served as a director of Flagler’s hotel company), and to her two sisters. Time wore on and times changed, but the Kenans’ commitment to providing quality service did not waver. Although considerations prompted the selling of various properties, The Breakers continued to twinkle like a bright, previous star among the multitudes.

A second fire, in 1925, reportedly started by a “new-fangled” curling iron, again destroyed this crown jewel. But like Flagler before them, his heirs ordered an immediate rebuilding. Architect Leonard Schultze, the man later responsible for the design of New York’s famed Waldorf Astoria, was called in to create the new hotel. “With such a magnificent site,” he remarked, “it was worthy of nothing less than an Italian palace.”

Taking his cue from the Villa Medici in Rome and a palace in Genoa, Schultze designed the elegant structure that is the modern Breakers. More than 1,200 workers, including 75 artisans from Italy who crafted the stunning frescoes, put forth their best efforts. Within 11 months, The Breakers was once again welcoming guests under William R. Kenan’s careful guidance.

Upon his death, Mr. Kenan left his estate to establish the W.R. Kenan, Jr. Charitable Trust for educational and related purposes. The Breakers and other properties, he left to his sister’s children and cousins among the Kenan clan. Eventually, control of The Breakers passed to Frank Kenan and his brother, Jim. The Ponce de Leon was donated for use as a college under the instigation and leadership of Kenan relative Lawrence Lewis, Jr.

At both these landmarks, the legacy continues. The Ponce de Leon, with the help of a $19 million renovation, has become Flagler College, a small (total enrollment is 1,100) liberal arts school that provides a fine education amid amazing surroundings.

At The Breakers, meanwhile, Flagler’s dream of an American Riviera continues. The reins are passing to a third generation of the family: Frank’s sons, Tom and Owen, and his nephew, Jim. Recognition of changing times has brought modernization: air conditioning, a year-round season, and readily available fax machines and computers among them. The modernizations will continue as part of the quest to provide the best. But what hasn’t changed—and likely never will—is the desire to keep this grand dame of hotels, always, the “incomparable Breakers.”

“We all feel The Breakers is something that’s irreplaceable,” notes Owen Kenan, “and that it provides a tremendous opportunity we should maximize. As my father says, ‘The Breakers is like a great family jewel to treasure and guard.’”

Like Henry Flagler when he arrived in St. Augustine, the Kenans were not hotel builders. But they have, like Flagler before them, what it takes to maintain and enhance this unique hotel franchise located in one of the world’s great resorts. The great tradition of Henry Flagler continues with a new generation.