Sunday Favorites: The Havana Race

The 1935 start of the Havana Race. Photo: Florida historic archives.
The 1935 start of the Havana Race. Photo: Florida historic archives.
Merab Favorite
ST. PETERSBURG — In 1952, a fleet of 29 sailboats participating in the St. Petersburg to Havana Race crossed the finish line only to encounter a spray of bullets to their sails and rigging. This was an alarming surprise considering they were usually given a complimentary bottle of rum and gratis water-taxi ride to a lavish after-party upon their arrival in Cuba.

That year the welcome party that normally greeted them at the docks with drinks and music was replaced with solemn Cuban troops wielding firearms. A U.S. Coast Guard cutter that escorted them along the way strongly urged the sailors to return to the states immediately, but the party went on. It was the first sign of upheaval on the island of Cuba, at least, from a sailor’s prospective.

At the time, there was political and military strife while Col. Fulgencio Batista overthrew the current president Carlos Prio Socarras. According to an All at Sea article, "St. Petersburg to Havana Race," Batista had expertly planned his government seizure to coincide with the regatta as a way to gain international press. (Batista’s short-lived dictatorship was eventually defeated during the Cuban Revolution.)

It was the beginning of the end of the St. Petersburg to Havana Race, a cherished local tradition that ran for nearly three decades.

Originally, the race was a promotional event thought up by yachtsman and Chamber of Commerce businessman George 'Gidge' Gandy Jr. He wanted to bring the City of St. Petersburg out of its two-year slump following the real estate bust and stock-market crash of 1929.

Gandy had sailed to Cuba that year on the 36-foot ketch Cynosure and had thoroughly enjoyed his trip. He reached out to members of both the St. Petersburg Yacht Club and the Havana Yacht Club to organize what he believed would become a world renowned regatta.

But Gandy wouldn't be satisfied until he had the most established yachtsmen sailing in the race. He began a "letter campaign," engaging all the wealthiest sailors on the East and Gulf coasts. If he didn't receive a letter of refusal, he wrote to them again.

On March 30, 1930, a gun boat started a fleet of 11 yachts headed for Havana. Spectators crowded the St. Petersburg Municipal Pier, watching the boats tack closely to the structure before crossing the starting line at the boom of a shotgun.

It was a rough trip: a 284-mile course on three bodies of water. Tampa Bay marked the first 17-mile leg, followed by 180 miles into the Gulf and then 90 miles across the Gulf Stream. But the view after the treacherous crossing was one that would last a lifetime. Morro Castle was a sight to behold on a moonlit night, one the sailors enjoyed while anchored off the coast.

The commodore of the Havana Yacht Club oozed hospitality. Sailors attended a lavish awards banquet where the President of Cuba himself, Gen. Gerardo Machado, presented the winner with a huge silver medal.

Back then, a trip to Cuba was about as easy as jumping on the Fast Cat to Key West. The wives and girlfriends of the sailors would take a steamship over that day and meet their seafarers at the awards ceremony, usually staying at a world-class hotel following the celebration.

It wasn’t long before the regatta gained national attention and attracted some of the most established sailors like Charley Morgan, of Morgan Yachts and Ted Irwin, of Irwin Yachts. By 1935 participation had doubled with yachts hailing from all over the world. It was covered in national magazines and journalists traveled from afar to see the finish in Cuba.

However, WWII took a toll on the event. In 1941 the fleet was reduced to eight. There were no more races until 1946.

After the war a new generation of sailors took over. They were fearless, reckless and sailed smaller boats than the yachts their fathers captained. Improved technology allowed for better communication onshore.

In the 1950s, WSUN broadcasted the race from the Municipal Pier, but one year, when John Wilhelm gave an account of his current situation, saying "If the wind holds we'll soon be down on Rebecca, we’ll ease the sheets and really drive her home," he found himself in hot water. Listeners were absolutely appalled, according to the St. Petersburg Yacht Club Centennial publication.

Wilhelm was quite the prankster. One year, he invited some Cuban sailors he’d met during the race back home to St. Petersburg. Wilhelm owned a funeral home and when the city bars shut their doors he opened his business up to his new friends. One young Cuban man passed out in the funeral home only to wake up the next day in one of the caskets!

Two days before the 1958 regatta, Fidel Castro’s revolution demanded a course change which had the sailors finishing in Miami. The next year, Havana marked the finish line once again, but gun-wielding militia put a damper on the party scene. It was the last legal race to Havana in the 20th Century.

During the 1990s, the St. Petersburg Yacht Club tried to revive the regatta, applying for embargo exemptions for 20 yachts, but when government officials refused and Cuban-American protests began breaking out, the board of directors unanimously abandoned the endeavor.

But the new millennium shines a new light on the memorable event.

As relations with the U.S. and Cuba improve, talk of resurrecting a historic local sporting event has emerged. The commodore of the St. Petersburg Yacht Club is hoping to bring it back as soon as next year and I'm looking forward to hearing the sail tales of an entirely new generation and their Cuban adventures.
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