Snuggled firmly in the middle of Nassau, Bahamas, Graycliff is a sprawling “grand estate” built by privateer John Howard Graysmith in the 1700s. It became Nassau’s first official inn in the mid 1800s, and has been enticing visitors ever since. Sporting beautiful rooms, a virtual museum of antiques and art covering nearly every inch of space, a relaxing garden, and a five star restaurant, I can easily envision myself staying here – and I haven’t even touched upon cigars yet. 

Graycliff was originally brought to my attention by my wife, who wanted to go on vacation to the Bahamas for our honeymoon. We booked a stay at the estate as part of our cruise, but unfortunately the days leading up to the cruise saw the birth of a hurricane barreling directly in our path. Lovely Florida. In one of my less manly moments, I decided to reschedule our trip and save my sea legs for another day.

I’ve always been a history buff, with a slight interest in the nefarious deeds of pirates thanks to Walt Disney, who made murdering, pillaging, and foul language into good old fashioned family fun. So when my wife pitched me on the idea prior to our ill-fated hurricane experience, she did so by informing me of an old estate she had visited there once that was founded – you guessed it – by a pirate.

Graycliff has a very rich history that extends beyond piracy, into the Civil War, and even has a link to mobster Al Capone and royalty, but I would be hard pressed to fit a third of it into this article. Instead let’s focus on the aesthetics, offerings, and most importantly, their cigar package.

Graycliff Cigars 

Graycliff is currently owned by cigar enthusiast, Enrico Garzaroli. Long enamored with cigars, Garzaroli brought Cuban torceador Avelino Lara on board to help create the signature Graycliff brand.

The Graycliff line of cigars consists of 11 brands, including the Label series (Red, Blue, Pearl, Green, Black, Purple, and Yellow), as well as the Bahiba Original, Bahiba Reserve, Big Bamboo (a whopping 18” cigar), and the Junkanoo.