Experience the Iconic Rum Runner in the Florida Keys

In the Keys, we embrace a laid-back “It’s 5 o’clock somewhere” mentality, making our island chain the perfect source for some wonderful libations. One standout is the legendary Rum Runner, a cocktail with a rich history and a unique flavor profile.

The Origin of the Rum Runner

Our featured cocktail, the Rum Runner, was allegedly invented by John Ebert, also known as “Tiki John,” at the Holiday Isle Tiki Bar in Islamorada (now the Postcard Inn) over 40 years ago. Faced with an excess of rum and other liqueurs, Ebert mixed banana liqueur, Meyers rum, brandy, and grenadine, creating a drink that has become synonymous with the Keys.

Photo// www.eatyall.com

A Historical Nod to Rum Runners

Named after the rum smugglers of the early 1900s, Rum Runners were the aquatic equivalents of prohibition-era bootleggers. They transported alcohol by water, evading authorities and playing a pivotal role in the region’s history. Join our Key West Food Tour to learn more fascinating tidbits and visit historic spots tied to this era.

Try a Rum Runner on Our Tour

On our tour, you’ll sample the Rum Runner at the famous Rum Bar at the Historic Speakeasy Inn. Enjoy this fresh, fruity cocktail on their wrap-around porch, perfect for people-watching. The Speakeasy Inn, once home to Raul Vaquez—a Rum Runner between Key West and Cuba—still operates as a charming bed & breakfast with five historic rooms.

The Speakeasy Inn was the home of Raul Vaquez, who worked for the Gato Cigar Factory (where you’ll also visit on Key West Food Tour) and was a Rum Runner between Key West and Cuba. Another local and visitor favorite at the Rum Bar is the Painkiller, try one…or 2! This place is a local landmark – STILL serving as a small bed & breakfast hotel with 5 historic rooms?

Rum Runners on the Southernmost Food Tour

Additional Places to enjoy a Rum Runner

• Southernmost Beach Café: Cool off with a Rum Runner (on the rocks or frozen) right on the beach with your toes in the sand.
• Rum Row Bar at the Gates Hotel: Relive the prohibition days with specialty rums and cocktails by the poolside.

Discover the Legend of Capt. Bill McCoy

One of the most notorious rum runners, Capt. Bill McCoy, inspired the phrase “The Real McCoy.” He smuggled rum from the Bahamas into South Florida, evading the Coast Guard by transferring rum to smaller boats three miles offshore. This area became known as the “Rum Line,” with vessels lined up in “Rum Row” to collect their illicit cargo.

This brings us to our next stop, the Rum Row Bar at the Gates Hotel where you can channel the days of prohibition and specialty rums and rum cocktails…poolside.

Photo// Gates Key West Facebook Photos

Make Your Own Rum Runner at Home

If you can’t visit Key West soon, recreate the magic with these homemade Rum Runner recipes (courtesy of wikihow.com):

Standard Rum Runner

1 oz Pineapple Juice

1 oz Orange Juice

1 oz Blackberry liqueur

1 oz Banana liqueur

1 oz Light rum

1 oz Dar rum

Splash of Grenadine

Garnish lemon/lime/cherry

Fancy Rum Runner

½ oz Blackberry brandy

1 oz Banana liqueur

1 oz Light rum

1 oz Spiced rum

Splash of Orange juice

Splash of Sweet & sour mix

Garnish lemon/lime/cherry

Islamorada Rum Runner

1 ½ pz White rum

¼ oz Banana liqueur

¼ oz Blackberry brandy

½ teaspoon Grenadine

5 oz Sweet & sour mix

Top with 151 proof Rum

Garnish lemon/lime/cherry

LIKE IT? PIN IT!