Editor’s note:  Russ Hoadley, my friend and fellow sailor, graciously wrote this story about sailing to Cuba in the Pensacola a la Habana Race.  Please enjoy this very first guest post on Sailing with Steve.  You can reach Russ at rhoadley2@yahoo.com.

HAVANA, Cuba – This sun-drenched island has changed from 15 years ago when I first raced here aboard Mac Smith’s 44-foot Lafitte Twilight (from Daytona Beach, FL).

This time I’ve had the privilege of being on a crew of eight on XTC, Tom Glew’s 46-foot Beneteau (from St. Petersburg, FL) that made a clean sweep in May of a race to Isla Mujeres, MX (1st in class, division and overall).

The event that has brought us here is the first-ever Pensacola a la Habana

Russ Hoadley at the helm

Race, one of a growing number of yacht events to the Communist isle since the Obama State Department began to relax the embargo. 

Havana shows signs, albeit halting, of rebirth from the 50-plus years of decay which came with the Castro Revolution, Russian missile crisis and subsequent U.S. embargo. Some elegant old-world buildings have been buffed up. Many others still are moldering away.

We’ve just finished five days of hard sailing, hammered by squalls, plagued by electronic and mechanical gremlins, and still we will collect first in class and division at the awards party.

We are at the enormous but deteriorating Marina Hemingway, 15 miles west of the storied old city. Hemingway International YC is our host, with

Street musician Angel Kindelan

Comodoro Jose Escrich doing his effusive best to make us feel welcome. A roast-pig dinner and exotic entertainment by undulating dancers are to follow. 

The 500-mile slog here started in uncertain weather in Pensacola Bay at 0800 Saturday, Oct. 31. Twenty-one boats in five classes reached east across the bay, then beat out the channel in 15-20 knots from the southwest. Squalls were predicted as we eventually locked into a long starboard tack, and the forecast was not wrong. Through three days, sporadic downpours occurred with winds into the high-30s.

Day 4 brought an expected southeast shift, allowing a tack onto port past the Dry Tortugas, Havana now just 90 miles away.

XTC heads into more squalls

After pounding through the night across the Florida Straits, we finished in a squall at the hard-to-find sea buoy. Soon we were led through the reef-shouldered channel to smooth water, a lengthy but courteous Customs check-in and a berth with modern hook-ups. The nearby hotel was visibly doggy (crumbling façades, uncertain water, no toilet paper), but the marina itself was quite satisfactory.

Our five days in Havana were a kaleidoscope of colorful old Chevys, Buicks and Fords, deluxe night clubs, sensuous dancers, magnificent cigars and rum, lyrical music and historical and revolutionary stories.

Cubans we met seem pleased with their country’s progress even as they acknowledged the scarcity in their lives. “Money isn’t everything,” said Carlos, a philosophical 47-year-old father of two. He is a taxi-driver, a self-educated man who takes quiet pleasure doing triathlons with his sons and his girlfriend.

Cubans were cheerful, fit, hard-working, friendly, smart people who love their land, their culture and music, their families and friends … and their languid, long-playing way of life. It rubs off easily on us.

Visits to the Museo de la Revolucion and the Plaza de la Revolucion underscored how important the six-year uprising was to these people 50 years ago. They seem to revere the Castro brothers, along with Che Guevara and Camilo Cinfuegos, the leaders of the conflict that toppled Fulgencio Batista in 1959.

A tidal wave of change appears on its way to them now, as tourism swells, and thousands – perhaps millions – of Americans jump the barriers to visit this land of sun, rum and music.

As we cleared out of Cuba Customs and looked back at the Havana skyline, a gunboat shadowed us, reminding that normalcy has not fully arrived.

We felt the pull of the island. We were pleased to be in the vanguard of sailors who are leading the way. We will be back.

Crew celebrates victory – front: Loren Hoffman, Adam Gautier; rear: Hank Brautigam, Russ Hoadley, Ron Gagne, Tom Glew (skipper), Tony Dimattia; not shown: Charlie Marts