Al Capone once lit up here. So did Winston Churchill and a whole slew of pirates. But those aren’t the only reasons for the dedicated cigar-smoker to experience Graycliff’s warm Bahamian charm.

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It’s hard to resist Graycliff’s tropical charms — particularly when you walk into your room and find a bottle of fine scotch and a large ashtray holding matches, cigar cutter, and a hand-rolled Churchill. The room was large enough for me to park a good-sized car. Fortunately, my car stayed in Manhattan, along with New York’s utterly ridiculous smoking regulations, so I lit up with aplomb.

Graycliff was one of Nassau’s first Inns, built by Captain John Howard Graysmith when the area was still a pirate haven. It hosted such legendary figures as Al Capone, King Edward III and Sir Winston Churchill until its purchase by Enrico and Anna Maria Garzaroli in 1973. The Garzarolis transformed Graycliff from teardown to a celebrity-magnet resort with an award-winning (and five-star) restaurant.

Enrico Garzaroli is a gentle giant of a man more than capable of chatting on a range of topics in at least five languages. One of the most favored topics is wine, and no wonder: In the belly of Graycliff sits the third largest privately owned wine cellar in the world (and a former 19th century prison), with some 275,000 bottles gathered from over 4,000 vineyards, including a 1727 bottle of Riesling worth approximately $250,000 — the oldest vintage wine in the world.

But the true gem here may be Graycliff’s own cigar factory, where a handful of Cuban cigar rollers sit in a smoky but well-lit room making sticks for the much-lauded Graycliff brand, developed by Enrico and master torcedor Avelino Lara (once Fidel Castro’s personal roller). Graycliff’s cigars include the Chateau Grand Cru President, a full-bodied range (blended from aged Costa Rican, Nicaraguan and Honduran tobacco) with a spicy aroma that smokes well to the end. Also recommended is the white-labeled Crystal, a medium- to full- bodied cigar with a sun-grown Ecuadorian wrapper and a blend of Honduran and Nicaraguan tobacco. Sit in one of the resort’s 20 rooms or beside one of its two pools, pour a glass of wine and light your cigar, and then fall under the spell of Bahamian hospitality.

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