There is a place in the Bahamas where one can eat artisanal chocolate, walk on 300-year-old hand-painted tiles, buy handmade cigars, eat fresh-baked pizza, survey one of the world’s most storied wine cellars, and even spend the night, soaking in the estate’s sounds and picturing its past. Graycliff, as it is known, is located on Nassau—the country’s capital city and 11th-largest island—and its history is an intriguing one.
The site originally held Nassau’s first Anglican Church, built by Governor Nicholas Trott in 1666; in 1703 the structure was demolished by the Spaniards, but surviving parts have been weaved into the existing Graycliff building. Local legend has it that the mansion was first built by the famous pirate Captain John Howard Graysmith in 1740; in the 1920s, it was owned by Polly Leach, a close friend of Al Capone’s; in the sixties, it played host to nobility including the Duke of Windsor (previously King Edward VIII) and Sir Winston Churchill.
Now it is an AAA-Four Diamond-rated hotel (with the first pool ever built in the Bahamas) with the Caribbean’s first five-star restaurant, a cognac museum, a cigar company, and a chocolate factory. Rich in culture and unafraid of its past, Graycliff is where worlds collide. In the Graycliff Cigar Factory, tobacco is hand-rolled into those classic thick sticks, and it is not uncommon to see an employee smoking one himself while working. The cigars are aged for nine months in an on-site humidor, giving them that classic smoky flavour. Avelino Lara, once the personal roller for Fidel Castro, used to make cigars at Graycliff. Indeed, if only these walls could talk.
Below ground, down a set of steep stairs and with ceilings so low even the average person has to duck, sits one of the most celebrated wine cellars—the third-largest, in fact—in the world. One could easily get lost down there among the narrow halls and array of bottles, many of which are covered with a layer of dust, untouched for years, too precious to pour. The cellar holds over $20 million worth of wine, including a bottle from 1727—the oldest remaining one on the planet. Down there between the brick and grape is Hudson Clark, a man affectionately known as Clarky; he is Graycliff’s cellar keeper and sommelier, and his knowledge, which he uncurls from a mouth of missing teeth, is vast. “We have a system in place so that everyone can be smiling and laughing,” he says with a playful grin. “That’s what it’s all about: keeping you smiling even after you spend that $28,000.” The cellar has a private dining room where multi-course dinners are paired with bottles from around the world—even Michael Jordan has visited, and it is amusing to imagine his tall frame squeezing through the tiny chambers. There is money to be spent at Graycliff, certainly, but there are unforgettable experiences to be had, as well. “They say the main thing about life is happiness,” says Clarky, as he moves about the cellar. “So when you’re happy, you’re happy—right?”