Thursday, April 16, 2026

Exploring Old Town Key West’s Distilleries and Breweries

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 LagerKey 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. 

No comments: