Nassau’s most characterful hotel is this 260-year-old home, built by a wealthy pirate. Hidden above town on West Hill St, the Georgian main house is filled with high-ceilinged rooms, musty antiques, mismatched oriental rugs and intriguing nooks and corners begging further exploration. Huge gardenside cottages, arrayed around an extraordinary Spanish-tiled pool, are equally alluring.

　　The astonishing wine cellar (250,000-plus bottles!) and a library redolent of the rich aroma of Cuban cigars have kept guests such as Winston Churchill and The Beatles happy. There are two main buildings on the grounds: one is the hotel itself, which includes the Graycliff Restaurant, and the other contains the steakhouse Humidor Churrascaria and the Graycliff Cigar Co.