
In 1920s Key West, the Florida Keys Over-Sea Railway steamed regularly into town, carrying passengers from mainland Florida and points farther north. Pan American Airways launched the first international airmail service from Key West to Havana in 1927, followed in 1928 by passenger service between the two cities.
Dance marathons were all the rage at Key West hotspots like La Brisa, and Ernest Hemingway spent the winter of 1928-29 on the island working on his novel “A Farewell to Arms.”
Of course, the period from 1920 to 1933 was also characterized by Prohibition, the nationwide ban on the U.S. manufacture, transportation and sale of alcoholic beverages.
In end-of-the-road Key West, however, much of the free-thinking populace regarded the ban as an annoying government exercise — and spent considerable energy devising ways to get around it.
Rumrunners in fast boats imported contraband liquor from Cuba, playing a daring game of “catch me if you can” with the federales. Key West’s former Cuban Consulate property became home to an infamous rumrunner, who supposedly built a second structure there to hide rum storage tanks.
Whiskey and rum were sold at illegal speakeasies, where in-the-know patrons could slip secretly inside to slake their thirst. One such speakeasy, which also offered gambling, featured a balcony railing carved with an identifying design of bottles and card suits.

On Dec. 5, 1933, much to the delight of cocktail connoisseurs in Key West and around the United States, Prohibition was finally repealed. Speakeasies reinvented themselves as legitimate saloons, where alcohol could be enjoyed openly instead of illicitly, and rumrunners sought less hazardous professions.
At Bar 1, the welcoming watering hole at the Key West Cooking Show’s historic 291 Front St. venue, the Prohibition era and other aspects of the island’s colorful past are spotlighted in an intriguing sip-and-learn experience.
“Key West History through Craft Cocktails” is a libation adventure guided by skilled mixologists. Sharing insights into cocktails that represent Key West milestones and highlights, they teach attendees to measure, mix, shake and savor the featured drinks.
Participants learn about Key West’s naval heritage and the intriguingly named Fly Navy Grog, the Curry Old Fashioned that commemorates an early leading citizen, the Key Lime Pie Shooter that salutes the local-born dessert, and other concoctions connected to the island city.
By the time the experience ends, attendees have enjoyed the featured cocktails with fellow “students,” learned how to craft them for friends and family, and developed a new appreciation for Key West’s vibrant heritage. Reservations are required for the lively libation adventure; call 305-294-COOK.
Last Call
Drink of the month: Hurricane. Tropical storms and hurricanes have occurred throughout the Florida Keys’ history — and residents respond with resilience, heart and spirit. The bold hurricane cocktail symbolizes their strength with ingredients that include light and dark rum, passion fruit syrup and fresh lime juice.
Event of the season: Chef Norman Van Aken, widely hailed as Florida’s culinary icon, presents an exclusive dining experience Friday, Dec. 5, at the Key West Cooking Show venue. Guests will both learn from the legendary chef and savor his cuisine in an intimate setting. Seating is limited and reservations are required; visit keystix.com.
Thirsty for more? Visit keywestcookingshow.com.



















