Key West is known for its many interesting features such as home to the Southernmost Point in the Continental US, Truman's Little White House, Hemingway's House & the six-toed cat, roosters, and drinking. Yes, this is mostly the irresponsible variety but for those who are more responsible, there are five craft beverage establishments on the key that are worth a visit.
Key West was also home to America's first overseas air transport flight when on October 19, 1927, a Pan American World Airways Fairchild FC-2 floatplane delivered mail from Key West to Havana. From that date until its "collapse" on December 4, 1991, Pan Am was the principal and largest international air carrier in the United States. In Key West tickets were sold out of their building on 301 Whitehead Street and since the company's closure has operated as a brewpub first under the ownership of actress Kelly McGillis (Kelly's Caribbean Bar Grill & Brewery) and now as
First Flight Island Restaurant & Brewery. This brewery has a core lineup of beers that cater to the tourism market - an Amber, IPA, and Wheat ale; but they also produce a limited release series where the best action occurs. The
Czech Engine Pilsner is spot on and their
Beach Day IPA is a juicy blend of tropical fruits. For dessert hope the
Midnight Landing Honey Porter or
Nuts & Bolts Chocolate Peanut Butter Ale are on tap.
As its name implies,
The Waterfront Brewery overlooks the Key West Historic Seaport and Bight and operates as a brewery, restaurant, and a licensed wholesaler of Florida Keys finfish and shellfish. The brewery offers a strong portfolio ranging from an
Island Life Lager to the
TruMan Double IPA. Both of these are well made, the first a refreshing quaffer, the second a rather smooth and complex offering. However, our two favorites were the
Key Lime Gose and
Lazy Way IPA - both provide tropical flavors with the kettle-soured Gose tart and refreshing while the Lazy Way is a juicy, juicy IPA.
Being so close to the Caribbean Key West is practically synonymous with rum and the first place to imbibe is the
Key West First Legal Rum Distillery -- opened in 2012 by Chef Paul Menta and Tony Mantia. The distillery is housed in a building built in 1900 that was the original location of Jack's Saloon and once a Coca-Cola bottling facility. Today the building houses distilling equipment that cranks out several styles of rum from a clean white to flavored to a high octane
105 Simonton Rum. The rums are produced by fermenting sugarcane juice which is then generally distilled six times. If the rum is aged they use salt-cured barrels and when flavored they utilize locally-sourced food flavors. Our overall favorite was the
Aged Key West Raw and Unfiltered Rum ($63) aged in new American oak barrels. The distillery never uses previously used barrels and instead purchased #3 charred barrels which they fill with fresh seawater. Overnight the barrel expands and in the morning the water is drained and the barrels cure in the sun. The salt residual opens the pores of the wood allowing the rum to soak up more of the wood nuances such as fig, plum, vanilla, and pepper. This raw and unfiltered rum definitely has these characteristics as well as a bit of funk - that makes it truly unique. This make is compatible with a Dark and Stormy and even more compatible by adding grapefruit juice to that cocktail plus a little lime. The other rum we purchased was the
Cuban Coffee Rum ($35) where dark roasted coffee beans are aged in rum barrels to create a coffee extract. Then Demerara sugar is toasted and added to the coffee in order to create a "true Key West Colada Cafe". The rum is savory and we've used as a morning quick start or an evening dessert.
The island also features two other distilleries that we were unable to visit.
Papa's Pilar Rum is also located on Simonton Street and concentrates on one iconic rum brand named after the famous author and his fishing boat.
Key West Distilling just moved to the Stock Island Marina Village and goes beyond rum by also producing whiskey, vodka, and gin -- the latter two using Florida sugar cane. Next trip to the Keys. Cheers.
Exploring Key West’s craft beverage scene is unusually simple thanks to the close proximity of several notable producers. Within a short walking radius in Old Town, visitors can move from two rum distilleries to three breweries while learning about the history behind each brand and the products they make. Key West Legal Rum, Papa’s Pilar Rum, Southernmost Pint Brewpub, The Waterfront Brewery, and First Flight Island Restaurant & Brewery each offer a distinct perspective on local production, yet all are easy to visit in a single, unhurried loop.
Start your tour along the harbor at The Waterfront Brewery and enjoy lunch and a flight watching the boats sail in. The brewery opened a decade ago and produces a wide range of beers including pilsners, IPAs, porters, and rotating specialty releases. Its production facility and taproom share the same building, allowing guests to see the brewing equipment while sampling the core lineup. Their Crazy Lady Blonde Golden Ale is a stable throughout the island and you can probably find Island Life Lager in several establishments - definitely at Hanks. For my money, go with the Danny Gunz ESB (Extra Special Bitter).
Head west from the harbor and enter the life of Ernest Hemingway. Papa’s Pilar Rum is named after Hemingway’s famous boat and the brand was created to reflect the writer’s connection to Key West and his global travels. The distillery occupies a former naval warehouse and produces blended rums sourced from multiple regions, aged and finished on-site. Core products include the Blonde Rum and Dark Rum, each with defined profiles shaped by solera-style aging and barrel finishing. I highly recommend the tour which provides excellent information on the history of molasses and rum production through the eyes of the British Navy and American colonists. 
The tour turns to Hemingway's life and how the distillery incorporates various aspects such as the unique bottle shape -- mimicking Hemingway's GI canteen. Apparently he carried two canteens, one filled with rum. The visit ends with a sampling of several expressions including a Rye finished rum and Sherry finished rum. My favorite was the Papa's Pilar Flagship Blonde Rum which is sourced from several sources from the Dominican Republic, Venezuela, Panama, and Florida; then Solara blended and finished from ex-Bourbon barrels and Spanish Oloroso Sherry casks. Enjoy neat to savior the vanilla and banana notes or in a Mojito. 
Key West Legal Rum was founded by chef and entrepreneur Paul Menta and operates out of a restored 1900s-era tobacco warehouse -- just a block away from Papa's Pilar. The distillery focuses on small-batch, pot-distilled rums made from Florida sugarcane. Their lineup includes the Key West First Legal Rum (a white rum showcasing the Demerara sugar cane), Key West Bad Bitch Rum Spanish Marie (aged in French oak barrels that held Pinot Noir wine for seven years.) and several flavored expressions that highlight local ingredients such as Key lime and coconut. Yet, their most interesting and tasteful product is the Key West Raw and Unfiltered Rum. It is aged in new American oak barrels with a #3 char where each barrel was cured in salt water from the ocean. As the salt dries on the inside of the barrel, it seals in and condenses the rich flavors of the charred American oak. This rum is very complex - lots cooking spices covered in honey.
Moving along, the Southernmost Pint Brewpub is only a few minutes away. Founded by Tadd Maudlin with the Blast Beer Company, the brewpub focuses on approachable, island‑appropriate beer styles. For instance, the 3.3% and fantastic English Dark Mild: Birmingham Pub. Include that beer in every flight. I continued with the Southernmost Pint Golden Ale, Heck Yeah Helles Lager, Key West Cream Ale, and Key Lime Gose Sour. All were delicious and right on style - particularly the Cream Ale which avoided the sweet lactose overdose of many versions and concentrated on crystal clear flavors. You won't find a stop with this range of delicious expressions. 
Finish your excursion with the longest segment -- passing Sloppy Joe's, Rick's, and Captain Tony's -- to First Flight Island Restaurant & Brewery. The brewery is located in the building where Pan American World Airways was founded in 1927, the site originally served as the airline’s first office and ticketing headquarters. Thus, expect an aviation theme. In that regard, before rebranding in 2017, the location was home to Kelly’s Caribbean Bar, Grill & Brewery -- owned by Top Gun actress Kelly McGillis. The brewery produces a core lineup of Old Havana Red Amber Ale, Capt. Maverick IPA, and the Sunset Clipper Citrus Wheat. Unfortunately the restaurant was hosting a wedding during our visit, so we detoured across the street to Hank's Hair of the Dog Saloon and a meal at Garbo's Gill paired with the Waterfront's Island Life Lager. 
What ties these five locations together is their accessibility. All are situated within a compact section of Old Town, eliminating the need for transportation and allowing visitors to move easily from one producer to the next. The short distances make it possible to learn about the history of each brand, understand the products they make, and experience Key West’s beverage landscape in a single, efficient route. Cheers to Key West and these unique craft beverage producers. 
