Graycliff 'G2' Maduro Pirate

The Graycliff G2 Maduro Pirate isn’t just a cigar — it’s a piece of Bahamian history with a story as rich as its flavor. The Graycliff estate began in 1666, when Nassau’s first Anglican church was built on the site. Nearly a century later, the notorious pirate Captain John Howard Graysmith retired from a life of plunder and built his grand mansion on the property in 1740. From that moment, Graycliff became a place of intrigue: a pirate’s refuge turned naval stronghold during the American Revolution, an officer’s mess for the West Indian Regiment during the Civil War, and later, a glittering playground for aristocrats and celebrities during Prohibition. By the 1960s, it was owned by European royalty, until Enrico Garzaroli acquired the property in 1973 and transformed it into the world-class resort and cigar-making destination it is today.

The Graycliff Cigar Company launched in the late 1990s, rolling cigars by hand in the resort foyer before expanding into international recognition. Today, the G2 Maduro Pirate continues that tradition of craftsmanship. Built with a foundation of Nicaraguan long-fillers and binder, wrapped in a lush Connecticut Broadleaf Maduro, it offers a medium-bodied profile layered with cocoa, earth, spice, and a touch of cream. Its balance of richness and smoothness makes it both approachable and deeply satisfying.

For a pairing worthy of its heritage, light up the G2 Maduro Pirate alongside a glass of Rémy Martin 1738 Cognac. The Cognac’s velvety body, with notes of dried fruit, butterscotch, and toasted oak, complements the cigar’s cocoa and spice while elevating its creamy finish. Together, they evoke the sense of old-world indulgence — a nod to Graycliff’s storied past and the pirates, princes, and pioneers who once walked its halls.

The Nicaraguan cigar industry originated when Cuban cigar makers escaped the revolution and re-established their livelihood in Nicaragua with Cuban-seed tobacco. Blessed with dark, rich soil, their new home was ideal for tobacco cultivation and Nicaragua quickly became known for cigars that rivaled Cuban quality. Unfortunately, revolution and war came to Nicaragua in the 1980s and devastated the industry, but it’s rebounded dramatically and is once again producing tobacco considered by many to be the finest in the world.

The Esteli Valley is in many ways the heart of Nicaraguan production and is known for its very powerful and spicy tobacco. The Jalapa Valley produces arguably the finest tobacco in the country: somewhat sweeter and less intense than Esteli, but extremely complex. The tobacco of the Condega Valley is often described as a blend of the other two regions.