That pink colonial mansion on West Hill Street, right across from Government House, has one of the most layered histories of any building in Nassau. Most people walking past it have no idea.

Built on the Bones of a Church and a Pirate’s Home
The land itself goes back further than the current building. The original site housed a church, but in 1703 Spanish raids led to a fire that heavily damaged it.
A pirate then built his home on top of the ruins. The mansion was originally built in 1740 by Captain John Howard Graysmith, who commanded the notorious schooner Graywolf and plundered treasure ships along the Spanish Main. The name Graycliff comes directly from him.
So the building you’re looking at today is essentially sitting on the bones of Nassau’s first Anglican church, with a pirate mansion built over it.
It didn’t stop there.
A Garrison, a Dungeon, and 275,000 Bottles of Wine
In 1776, when Nassau was captured by the American Navy, Graycliff became their headquarters and garrison. That’s why the wine cellar still has bars on its windows. That same wine cellar was reportedly used as a dungeon where prisoners were held, and it now contains over 275,000 bottles, one of the largest private wine collections in the world.


By 1844, Graycliff became Nassau’s first inn. During the Civil War it was commandeered again, this time as an officer’s mess for the West Indian Regiment while Nassau was running cotton and guns between the Confederacy and Britain.
Churchill, the Beatles, and a British Earl
Then the 1960s happened. Lord and Lady Dudley, Third Earl of Staffordshire, purchased Graycliff. During their ownership the mansion hosted the Duke and Duchess of Windsor, Lord Mountbatten, Sir Winston Churchill, Aristotle Onassis, and the Beatles. Churchill actually slept in what is now the Pool Cottage, and the Duke of Windsor was literally next door at Government House, serving as wartime Governor of the Bahamas.
In 1973, Enrico and Anna Maria Garzaroli purchased the property and turned it into the elegant hotel and restaurant it is today, the first five-star property in the Caribbean.
The Celebrity Traffic Never Stopped
The wine cellar’s private dining room is reportedly Mariah Carey’s favorite table in Nassau, and it’s also the room where Beyoncé and Jay-Z are rumored to have gotten engaged. Beyoncé has deep ties to the Bahamas through her father’s Bahamian roots, and the couple own two private islands here.
The guest list over the years also includes Nicholas Cage, Michael Jordan, Paul Newman, Bill Clinton, and Billy Joel, who once finished dinner and played an impromptu hour and a half piano set in the dining room.
So when people say Nassau doesn’t have history, point them to Graycliff: a pirate’s mansion, an American military garrison, a pirate dungeon, the Caribbean’s first five-star restaurant, a Civil War officer’s mess, a British aristocrats’ playground, and the site of one of the most famous rumored celebrity proposals in the world. All on the same plot of land, in that order.
See It in Person
Graycliff is a stop on KINDWalk, my guided walking tour through Nassau, in the latter half of the route. If you want the full story behind the pink mansion (and the rest of the landmarks most people walk right past) book a walk and I’ll show you.