Tasting Bars in Key West



It’s no secret that Key West loves to have a drink. Here you’ll find famous bars, historically famous drunks, and a good handful of distilleries, breweries, and one winery that make fascinating stops for our visitors. We’re sharing our recommendations for the best distilleries, breweries, and tasting bars in Key West.


Bars in Key  - First Legal Rum Distillery

Photo by Old Town Manor


Key West First Legal Rum Distillery | 105 Simonton St. | 305-294-1441
This distillery was established in 2012 at the original site of Jack’s Saloon in 1900 and the Coca Cola bottling plant in 1903. Free tours are scheduled at Noon, 1 pm, 3 pm & 4 pm Monday through Friday, 1 & 3 pm on Saturday and 3 pm on Sunday. There’s also a free Mojito class on Saturday afternoons at 4:30 pm. It’s both kid and pet-friendly. If you don’t want to do a tour, saddle up to the tasting bar anytime between 10am and 8pm daily.



On the tour, you’ll see the rum-making process, which spotlights sugar cane from Florida. The finished product specialties include Cuban Coffee Rum, Green Coconut Rum and Vanilla Brulee Dark Rum. They also offer rum cake, rum-filled chocolates, rum candles, shot glasses and T-shirts that make great souvenirs.


Key West Bars - Papa Pilar Rum Company

Photo by Old Town Manor


Pilar’s Rum Distillery, aka The Hemingway Rum Company | 201 Simonton St | 305-414-8754
Owned by the Heminway family, Pilar’s opened its doors in 2017 as a Rum Distillery and Experience Center. The building, itself, was built in 1878 as an all brick tobacco warehouse. They say they create their rum with the spirit of adventure that defined Ernest Hemingway himself. Pilar was named for Hemingway’s wife while he lived in Key West, and also his prized deep-sea fishing boat.



The family regularly donates profits to causes near and dear to the legend of Papa Hemingway, including The Ocean Foundation and International Game Fish Association. The rum products – blonde, dark and limited edition rums – may be purchased at the distillery along with a wide variety of other souvenirs, like clothing, glassware, and flasks. Guided distillery tours are $10 and last 30 minutes. They are available Noon to 4 PM daily, but you must be 21. The tour is free with any ticket from the Old Town Trolley or the Conch Train.


Key West wine

Photo by Old Town Manor


Key West Winery | 103 Simonton St. | 305-916-5343
Experience “Key West in a glass” at the island’s only winery. Choose from 43 varieties of tropical fruit wines, including their multi-award winning Key Lime wine, Hurricane White Sangria, and Mango Mama wine. The wines are bottled in St. Petersburg at the Florida Orange Groves Winery, designed for the Key West pallette. The showroom is bright and comfortable, nodding to Old Florida and all things Key West. The Key West Winery is open from 10 am to 6 pm Monday through Saturday and from noon to 5 pm on Sundays. Tastings are available throughout the day until an hour before closing time. Taste one wine for free, or buy a glass for $10 and sample any five wines.


Key West bars - Smuggler

Photo by Old Town Manor


Key West Smuggler Company | 627 Eaton St | 305-509-9775
Key West Smuggler Company is the brainchild of JD Martin, a Kentucky native whose family made bourbon whiskey for 136 years. When Jim moved to Key West, he dreamed of Kentucky Bourbon with a Key West appeal and created Key West Smuggler’s Bourbon Whiskey. He says that bourbon cannot be made here in Key West, as it relies on cold winters, something Key West has a major shortage of. So, his whiskey is distilled in his hometown of Owensboro, Kentucky at O.Z. Tyler Distilleries, using technology that creates a lighter, easier, fruitier bourbon that can substitute for rum in any tropical drink. You can check out the award winning bourbon for yourself, Wednesday through Sunday, at the Tasting Room.


Key West bars - Waterfront Brewery

Photo by Old Town Manor


The Waterfront Brewery | 201 William Street | 305-440-2270
In the Historic Seaport, on the waterfront at the end of the Harborwalk, you’ll find this brewery, restaurant and entertainment center. They brew a rotating selection of beers from shandys to pale ales to lagers and everything in between. Their signature selection is always on the menu: Crazy Lady (Honey Blonde), Lazy Way IPA and Island Life Lager, and many of these beers can be found in other popular bars in Key West. Their food menu features fresh seafood and fan favorites like burgers and salads. Happy Hour is from 4 to 6:30 daily and features half-price pints and flights of beer. Tour the brewery for free every Thursday, Friday, Saturday and Sunday at 5 PM. Tours may be booked online 24 hours beforehand.


Key West bars - First Flight

Photo by Old Town Manor


First Flight Restaurant and Brewery | 301 Whitehead St | 305-293-8484

First Flight is a restaurant and microbrewery with a famous past. Its location on the corner of Whitehead St and Carolina Stwas the birthplace of Pan American World Airways in 1927 and the first tickets were actually sold right there. Beyond the main red-bricked garden, and behind the French doors, is the Southernmost Brewery in the USA. You can sit at the Crash Bar, named for the Sikorsky Seaplane plunging through the ceiling, and enjoy one of their three original brews on tap: Havana Red, an amber ale, Maverick IPA, a medium pale ale, and Main Squeeze, a citrus wheat beer. No tours are offered at this microbrewery, but you can sample all three products in a flight at the bar. Happy Hour is from 4-6 daily with reduced prices on all the drinks and $5-$7 appetizers.




Take a tour, have a taste, have a drink, then look for your favorites in one of the countless bars in Key West. Cheers!

You can read our other concierge recommendations here, and check our availability for your stay in Key West here.