In the Keys we are known for the laid back “It’s 5 o’clock somewhere” mentality – so it’s only natural our Island chain is the source of some wonderful libations!

Photo// TheFeverentShaker.com

Our featured and favorite cocktail is the Rum Runner, which legend has it that it was invented by John Ebert or “Tiki John” at the Holiday Isle Tiki Bar in Islamorada (now the Postcard Inn) over 40 years ago. Allegedly, the bar had an excess of rum and other liqueurs that needed to be moved before the arrival of new inventory. So Ebert was challenged to concoct a cocktail, he mixed banana liquor, Meyers rum, brandy, grenadine, and the rest is history!

Photo// www.eatyall.com

The drink was named after actual “Rum Runners” that inhabited the Florida Keys in the early 1900s. Just like bootleggers during the prohibition era, Rum Runners smuggled alcohol, but instead of by land they went by water. If you haven’t been on the Key West Food Tour yet, our native guide can fill you in on some great tidbits from this part of our history, even show you some spots that played an integral part!

Also on our tour, you will get to sample one of the island’s most popular rum bars and Rum Runner at the one and only, Rum Bar at the Historic Speakeasy Inn. The fresh and fruity cocktail will go down smooth while you enjoy a seat on their wrap-around porch, taking in some prime people-watching while you’re at it.

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

Cool off at the Southernmost Beach Café with a Rum Runner or two – they offer it on the rocks or frozen. Even better, pull up a chair and enjoy it on the beach with your toes in the sand.

One of the notorious rum runners was a Capt. Bill McCoy, you may have heard of him before if you’ve ever used the phrase “The Real McCoy.” He smuggled rum from the Bahamas into South Florida.  The Coast Guard became privy to his tactics, so he would meet smaller boats about 3 miles offshore and transfer the rum.  This 3 mile limit was based on the U.S. jurisdiction over foreign waters and was soon called the “Rum Line,” while the vessels that lined up to take the product from McCoy were referred to as “Rum Row.”

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

If a trip to Key West isn’t in your immediate future, try your hand at your own homemade Rum Runner with these 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!