During the Prohibition Era, the well known connection was the smuggling of illicit liquor from Havana to Key West. The other side of the connection was a bit less known about and legal. Aeromarine Airway was running regular trips with their Model 75 flying boats to Havana carrying wealthy passengers to party and enjoy their liquor where there were no laws against its use.
For those with the means to fly and vacation in Havana, this was the best of all worlds for the drinkers of the era. The lavish cabarets of Havana in the 20's known for shows, gambling and most important the liquor. Fine Hotels all had the bars, cabarets, casinos and fine accommodations that the well to do required and didn't mind paying for.
This was a lucrative business taking the party minded people to and from Cuba. There were no laws being broken by going to Havana to party and the best of the best was out in the open. Unlike the speakeasies in the big cites in America where you ran the risk of being arrested if caught in one of the raids on the joints. It was luxurious and open to the public. Hemingway and Josie Russell were known to have visited Havana on their many fishing trips during prohibition, visiting many clubs in Havana. There were many other celebrities that visited during this period as well. Many of the upper class New York barmen were known to have moved to Cuba at the start of the "noble experiment" in order to make a living.
Bacardi redirected his promotional resources in a program with Pan American Airways later after the collapse of Aeromarine Airways to encourage "Prohibition parched Americans" to visit Cuba and soak up the sun and the rum in Havana. With slogans like "Leave the Dry Lands Behind" or "Fly with us to Havana and you can bathe in Bacardi rum in just two hours from now", they would lure the tourists in. All in all it worked very well, because they double the visits to Cuba from 45,000 to 90,000 visitor a year.
During this era, Havana became the number one tourist destination in the Caribbean, and remained on top until 1959 and the Castro take-over. This was a sad demise for a city that had so much going for it. In my visit last year I saw some of the remnants of the old night clubs and bars that made Havana so famous during the era. Most of them have fallen into disrepair, some like Sloppy Joe's are being restored. Said to be reopening this month in it's original location at the corner of Zulueta and Animas Streets in Old Havana, I'm looking forward to being able to belly up to this bar that I saw being reconstructed last September in the near future. Sloppy Joe's will be the only true Prohibition Era bar left operating in Old Havana.
This was a glorious era for Havana, one that led later to the American Mob taking over running the Gambling and prostitution, an era that ended with the Revolution in 1959. ;o)