History has it that the Graycliff mansion was originally built in 1740 by Captain John Howard Graysmith, a famous pirate of the Caribbean who commanded the notorious schooner Graywolf and plundered treasure ships along the Spanish Main. His buccaneering not only made him rich, but it also brought him fame and he was greatly feared for his famous exploits.
When Nicholas Trott became the Governor, during the second settlement of Nassau, in 1666, and joined by many Privateers and Pirates alike, he built the first Anglican Church in Nassau at Graycliff. It was destroyed by the Spaniards in 1703, segments of the ruins can still be seen and are incorporated in the Graycliff structure.
It is interesting to note that Graycliff witnessed the era when the Skull-and-Crossbones was the unofficial Bahamian Flag. Captain Woodes Rogers, the first Royal Governor of The Bahama Islands, attempted to bring an end to piracy. He acted as a privateer, which essentially was a legalized pirate backed by the British Crown, and helped restore trade. As a tribute to his feats, one of the guest rooms at Graycliff bears his name.
In 1776, when Nassau was captured by the American Navy, Graycliff became their headquarters and garrisons. Hence the bars on the windows of the world renowned wine cellar.
By 1844, Graycliff became Nassau’s first Inn ready to provide the traveler with genuine Caribbean hospitality; it was owned and operated by Mr. Nathaniel French.
Graycliff was later commandeered as an Officer’s mess for the West Indian Regiment during the American Civil War, it is important to note that during this time The Bahamas became headquarters for blockage runners selling southern cotton to British Mills in exchange for guns for the rebellious Confederacy. It is clear the West Indian Regiment secured the perfect recluse while America was involved in a hostile, bloody war. Closed to the public during this time, one can only imagine the fascinating war tales exchanged and countless barrels of rum consumed.
It was the age of Prohibition, where bathtub gin, Al Capone and the Charleston had their debut. During the roaring 1920s, Graycliff once again opened its doors to the public. It was then owned by Mrs. Polly Leach, a close companion to the heinous Al Capone. Needless to say, Graycliff was the most sophisticated gathering spot for the rich and famous.
Graycliff later became the private residence of a wealthy Canadian couple, Mr. and Mrs. I. Walton Killam. They had an equitable solution: summers in beautiful Montreal and winters in sunny Nassau. During their ownership, they completely renovated the mansion and constructed the swimming pool surrounded by lush tropical gardens next to the Pool Cottage. After Mr. Killam’s death Mrs. Killam stayed on at Graycliff until her death in 1964.
Royalty purchased Graycliff in 1966, in the personages of Lord and Lady Dudley, Third Earl of Staffordshire. During their ownership, Graycliff hosted such nobility as the Duke and Duchess of Windsor (formerly King Edward VIII), Lord Beaverbrook, Lord Mountbatten and Sir Winston Churchill. Lady Grace Dudley added a strict English accent to the decor and priceless collections of antiques, some of which still decorate the guest rooms and public areas.
Graycliff was purchased in 1973 by Enrico and Anna Maria Garzaroli who turned the private home into the elegant hotel and restaurant that it is today. In 2000, following an expansion, the Graycliff Cigar Company and the Humidor Churrascaria restaurant were added.
Graycliff is a landmark listed in the National Register of Historic Places.