The Graycliff Hotel & Restaurant Went From Pirate Hideaway To Baller Bahamian Retreat

An exclusive five-star destination known for Caribbean glamour, celebrity guests and fine food and wine.

The sunsets in the Bahamas are like no other, casting a rosy, golden glow over the crystalline waters of the Atlantic. Nestled amidst the vibrant city of Nassau lies a place where history, glamor, celebrities, fine wines, and cigars convivially—and sometimes sinfully converge—the storied Graycliff Hotel & Restaurant.

Built in 1740, this enchanting colonial mansion was once the private residence of Captain John Howard Graysmith, a notorious pirate who prowled the Caribbean. Over the centuries, it has transformed from pirate’s hideaway to naval garrison to a haven for nobility, including British royalty such as the Duke and Duchess of Windsor, who lived next door at Government House during World War II when the duke was Governor of the Bahamas. In 1973 Enrico Garzaroli (see sidebar below) bought the property and turned it into a luxury hotel with a focus on fine wine and cigars. It later became the first hotel in the Caribbean to receive the coveted AAA five-diamond rating.

The centerpiece of the property today is the five-star Graycliff Restaurant. Upon arrival in the parlor, guests enjoy their preferred cocktail before heading into one of five dining areas. Each dining room pays homage to the building’s colorful history. Walking the halls of Graycliff feels like stepping into a time machine. Antiques, curio cabinets, mahogany furnishings, and rare artwork offer a glimpse into the opulent past that has shaped this remarkable establishment.

Graycliff’s culinary offerings are a true epicurean delight, boasting a menu that showcases Bahamian and international cuisine. From crisp, citrusy conch salad to seared tomahawk ribeye, dining here is elevated by attentive staff and ambiance that exudes old-world charm.

One of Graycliff’s most buzzy features is its wine cellar—a paradise for oenophiles. Housing over 250,000 bottles from around the world, it’s a treasure trove for wine connoisseurs. The cellar is a living museum of vintages, with some bottles dating back to the 18th century. Feast your eyes on the third-largest private wine collection in the world, with some of the rarest vintages on earth, such as a 1727 Rüdesheimer Apostelwein and an 1865 Château Lafite.

Not to be outdone, the Graycliff Cognateque brings the study, collection, and yes, drinking, of cognac to similarly atmospheric heights. Home to Graycliff’s 9,000-bottle collection of cognacs, Armagnacs, ports and other spirits, the Cognateque’s offerings range from immaculate postprandial options to museum-quality investments like the 1893 Bottle #1 from A.E. Dor. Let’s just say it can get pretty spirited after dinner here.

For aficionados of the finer things, Graycliff boasts its very own cigar factory. Starting with a single Torcedore (cigar roller) working in the foyer of the restaurant more than two decades ago the Graycliff Cigar Company has unsurprisingly grown into an award-winning outfit employing over a dozen master rollers. Skilled artisans nimbly hand-roll cigars using traditional methods passed down through generations.

The result is a selection of cult status cigars renowned for their quality and lively flavor. Late into the night, high roller guests gather at guided tours of the factory, witnessing up close the meticulous craftsmanship that goes into each cigar. Afterward, kick back in your Bermuda shorts in the Cigar Lounge, and savor a freshly rolled cigar while sipping on a fine cognac or single malt Scotch.

Graycliff exudes an air of timeless elegance that has attracted celebrities from every corner of the globe. With its lush gardens, charming courtyards, iconic tiled swimming pool, antique-filled suites and cozy balconies, it’s no wonder stars like Pierce Brosnan, Jackie Onassis and Beyoncé have been spotted here over the years. The discreet, personalized service and luxurious accommodations create an aura of exclusivity that is simply irresistible. Graycliff is an icon of Bahamian luxury, uncompromising in its goal to provide the most magnificent guest experience imaginable after nearly three centuries of evolution.—Si Si Penaloza

Enrico Gazaroli Celebrates 50 Years Of Ownership & The Good Life At Graycliff

The story, as told by Enrico Garzaroli himself in Graycliff: 300 Years of Bahamian Luxury, the gorgeously-illustrated book about Nassau’s famed hotel and restaurant by Aaron Sigmond, is that he bought the historic mansion by accident in 1973, after a friend who took him to tea with Graycliff’s then-owner, a British aristocrat, misunderstood his intentions. He has never had cause to regret the purchase.

“Upon my first visit, there was a magnetism I will never forget; just like love at first sight, the house beckoned me,” Garzaroli later wrote. “I started to imagine what Graycliff would be like if I could fulfill my dream of creating a five-star restaurant and hotel where none existed.”

In fact he went above and beyond that original vision, adding a cigar company and a wine cellar that today houses over 250,000 bottles, to what would become Nassau’s first five-star property. “I started to do wine, liquor and cigars to enhance the experience of the clients,” as he put it.

Since 1986, Wine Spectator magazine has named Graycliff’s wine cellar as one of the best in the world, and Graycliff has won many awards over the years; culminating, most recently, in Enrico’s being given the prestigious Clement T. Maynard Lifetime Achievement Award, honoring tourism’s finest in the islands of the Bahamas.

“You only have to visit us once to know we constantly strive for excellence, from the cuisine and wines to the hotel amenities and service,” Enrico notes in the book. “As luxury hoteliers, our expectations for style and comfort are very high…. When we first opened our doors, we knew we had to wow the public—you only get to make a first impression once. We have the perfect location next door to Government House, which hosts international officials and many other visitors to our island country, but we’ve also made it a friendly place for locals.”

When his distinguished guests arrive, “They want the best possible experience,” Enrico said at the time of the tourism award. “The secret to my success is work—hard work. Never relax. Never believe that you have reached something because there is always somebody, somewhere, somehow that comes out with new ideas,” so you have to be one step ahead. “It’s really a pleasant challenge.”

“Quite simply put, Enrico Garzaroli is one of my favorite people,” Aaron Sigmond tells us. “A larger-than-life character, he is a rapscallion in the very best way possible—unquestionably a spiritual descendant of the buccaneer Captain John Howard Graysmith, captain of the schooner Graywolf and scourge of the Spanish Main, who had Graycliff House built in 1740. Garzaroli is a consummate host, who has assembled a wine and cognac offering nonpareil for his restaurant and hotel guests, to complement their Continental-Bahamian culinary arts dining experience; in addition to every other hospitality amenity imaginable.”—Jared Paul Stern

This article originally appeared in the Nov/Dec 2023 issue of Maxim magazine.