The first rule is, never call “Hurricane” Helen Fahey a bartender. Her title is “craft mixologist,” and it’s best to remember that, if you want to enjoy one of the straight-from-paradise cocktails she creates. Fahey does her magic at the recently opened Hemingway Social Club in Key West, where if you belly up to the bar, you’ll be doing so next to a life-sized statue of Ernest Hemingway, himself. Hurricane Helen loves her job, fashioning brilliant beverages from the rum produced on site at Papa’s Pilar Distillery, operated by the Hemingway Rum Company. The craft mixologist exudes the spirit of Key West — a Florida town known for its very serious commitment to making sure everyone is having a good time.

Craft mixologist “Hurricane” Helen Fahey, a Canadian, works her magic for satisfied customers. At top, “Cheers, friend!” Hemingway himself presides over the bar in the Hemingway Social Club. (Paul Knowles photos for VacayNetwork.com)
Maybe she brings that sense of hospitality from her hometown — she was born and raised in the heart of wine country, in Niagara-on-the-Lake, a tiny municipality in the Canadian province of Ontario. Though just a short drive from the natural wonder of Niagara Falls, the historic town is regarded for its quaintness and charm, qualities Fahey brings to the tip of the Sunshine State.
We relaxed over some amazing drinks, sharing our table with Hemingway Brand vice-president Tricia Flannagan, who told us the story of the distillery.
The name “Hemingway” is almost synonymous with Key West. Hemingway House, with its resident polydactyl (multi-toed) cats and authentically preserved writing studio, is the number one attraction. Although you might suspect that even more visitors spend time at each of the two bars associated with the famed novelist — Sloppy Joe’s and Capt. Tony’s. And each year, hundreds of wannabes compete in the Hemingway Look-a-like contest held in July during Hemingway Days.
But don’t assume that the Hemingway Rum Company adopted the name purely for branding purposes. In fact, explained Flannagan, the distillery is “licensed by the Hemingway family.” Royalties from the sale of the rum go to the Hemingway Foundation, which supports conservation and literary causes. And at least one Hemingway family member — grandson Patrick — is still “very connected” to the operation, usually visiting the distillery during Hemingway Days.

This photo of Ernest Hemingway as a boy, and a letter he wrote indicating his wish to be a writer, is on display on the distillery tour. (Paul Knowles photos for VacayNetwork.com)
The Hemingway Rum Company was founded in 2012. The brand’s “Papa’s Pilar” rum is named for his famous boat, the Pilar, which in turn was inspired by the nicknamed of his second wife, Pauline. It could be argued that Hemingway loved fishing more than he did writing, or any of his four wives. (Actually, that’s probably not true; as Tricia Flannagan pointed out, “He was a hopeless romantic.” Just not a very faithful one.)
It is well documented that he loved his cocktails, so the marriage of sailing vessel and beverages is a perfect fit. Hemingway’s nickname was “Papa” and, oddly, he adopted it when he was only 27 years old.
The distillery produces a variety of rums, all custom blends and “artisan crafted,” including Blonde, Dark, and Key West, plus special editions.

The still at the Hemingway Rum Company can be viewed as part of the distillery tour. (Paul Knowles photo for VacayNetwork.com)
The rums are excellent; the bottles that contain the spirit are collector’s items. A lot of creative thought went into the bottle design, which is modeled after a Second World War canteen, honoring Hemingway’s work as a war correspondent. His time on the battlefields had a distinctly Canadian connection — Hemingway was reporting for the Toronto Star. He is said to have carried two canteens at all times — one for water, one for rum.
The closure on the bottle is designed as a compass, a nod to Hemingway’s adventures on land, on sea … and in Key West, where he may have needed guidance to find his way from Sloppy Joe’s to his home on Whitehead Street.

This rather unassuming entrance leads the way into the Hemingway Rum Distillery in Key West. (Paul Knowles photo for VacayNetwork.com)
The company has come a long way in just over a decade. From small beginnings, the Hemingway Rum Company has become a major tourist attraction, drawing thousands of visitors to its shop and tasting room, and to regularly scheduled tours of the distillery. The place features all things Hemingway, from books to historic photos displayed all along the tour.
Although the Hemingway Rum Company began making rum in 2012, it was only recently that the company has evolved into its current state. Flannagan explained that the distiller could not sell cocktails until July 2021. At that time, distillers petitioned the government for a change in laws, and it was granted — with the intriguing proviso that the distiller could only create and sell cocktails using its own spirits.

The Papa’s Pilar Rum bottles’ design is based on Second World War battlefield canteens carried by then-newsman Ernest Hemingway. (Paul Knowles photo for VacayNetwork.com)
So you can’t get a gin- or vodka-based cocktail here, and that restriction opened a window of opportunity for craft mixologists like Hurricane Helen, who delights in using rum, herbs, spices, and other natural — usually organic — ingredients to create her masterpieces. Her magic takes place in the Hemingway Social Club, which in my opinion — having visited my fair share of bars in Key West over the course of many visits — is a unique and completely wonderful addition.
For one thing, it’s a relaxing space, unlike the very happening bars such as Sloppy Joe’s and the Hogs Breath Saloon. Hurricane Helen asked what I usually like to drink, and I mentioned my beloved single malts. I was astonished when she delivered a rum-based cocktail that actually exhibited all the qualities I enjoy in a dram of Macallan or Writers’ Tears.

Music veterans Terri White and Larry Baeder put on a show at the Hemingway Social Club. (Paul Knowles photo for VacayNetwork.com)
And the terrific music on offer suited the more laid-back vibe — we sipped to the jazzy sounds of guitarist Larry Baeder and singer Terri White, both highly accomplished veterans with impressive, eclectic resumes.
If you are planning a visit to Key West, you’ll enjoy a day spent following in the footsteps of Hemingway — soaking in the spirit of his writing studio, trying unsuccessfully to pat one of the multi-toed cats, visiting the sundry bars that claim connection with Papa. But be sure to give the most time to the Hemingway Rum Company. Take a tour, do a tasting, and then settle back and savor, in the company of Ernest, Hurricane Helen, and some fine musicians.