Race to Cuba: Havana Daydreaming

The crew of J/130 Lesson #1 prepares for the start of the first race to Cuba in decades.

October 29, 2015
Troy Gilbert

Back in December the U.S. government made the surprise announcement of the reopening of diplomatic ties with Cuba and I immediately said to myself, “Holy crap – we will be racing to Havana in 2016 or 2017.” No one would have guessed the remarkable speed with which Gulf Coast clubs and associations would put together and get approval for the return of these historic races to Havana and the Marina Hemingway.

With a legacy of races reaching back to the St. Petersburg YC’s Havana races in the 1930’s, Cuba has always been the exotic port of call for Americans and the history is as colorful as one would expect. The days of schooners may have passed, but in May, the Pensacola YC announced a surprise regatta and nearly six months later we are transiting a J/130 east through the Mississippi Sound towards Pensacola and a start on Halloween morning.

Cobbling together two mixed crews over the summer, including solo sailor Ryan Finn and 2014 Mallory Cup champion crewmember Randall Richmond, the eight of us marched Bob Seger’s (of the Silver Bullet Band fame) old boat through a bottom job, sail drive replacement, shroud, engine repairs, and untold other items including a new #3 Jib. Not to mention the piles of paperwork required by the U.S. State Department, Coast Guard and other agencies – the Cuban government having placed no such impediments on the crews whatsoever.


Lesson #1 has over the last 15 years primarily done beercan and Lake Pontchartrain races with a few 100nm Gulfport to Pensacola’s for good measure. This Saturday we sail south from Pensacola Bay towards this island so elusive to Americans and described by the first European explorers as “an island crowned in palms” and will put her to a task that she hasn’t done since the Mac Race in 1999.

Pairing up with the satellite communications company Globalstar, with shipboard wi-fi and sat-phones, the crew of Lesson will transect 500nm across the Gulf of Mexico and midway catch the downward arc of the massive Loop Current for a +2 kick straight to Havana.

As we slide east along the Gulf Islands of Mississippi and Alabama, the water is already becoming clearer as we lose the effects of the muddy Mississippi River and the sugar sand beaches of Pensacola will be in sight by sunset. Talk onboard is of the French and Spanish sailing this coast 500 years ago and of rum , particularly Havana Club Siete Anos – an email just came through on the Sat-Fi system confirming our reservations next week at the legendary Tropicana in Havana for the Saturday night after the prizegiving.


It may be a cliche, but cliche’s exist for a reason. With the legacy of Gulf Coast sailors landing in Havana for nearly a century behind us, this crew has worked their tails off in prepping this boat and deserves every bit of their Havana daydreaming over the summer. This Saturday morning we will hear the gun and only 500nm stand in our way to making that a reality

Follow along with the crew of Lesson #1 here for updates on the race to Cuba.


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